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Journal articles on the topic 'Stereoselective synthesis'

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Published: 4 June 2021

Last updated: 25 May 2024

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1

Akatan, K., Y. M. Suleimen, and Y. O. Tashenov. "Stereoselective synthesis of terpinen-4-ol-based aminoalcohols." BULLETIN of the L.N. Gumilyov Eurasian National University. Chemistry. Geography. Ecology Series 123, no. 2 (2018): 42–48. http://dx.doi.org/10.32523/2616-6771-2018-123-2-8-42-48.

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2

Moriya, Kohei, Kuno Schwärzer, Konstantin Karaghiosoff, and Paul Knochel. "Stereoselective Synthesis of Secondary Alkyllithiums and Their Application to Stereoselective Cuprations or Intramolecular Carbolithiations for the Stereoselective Synthesis of Alkylidenecyclobutanes." Synthesis 48, no. 19 (May 23, 2016): 3141–54. http://dx.doi.org/10.1055/s-0035-1562096.

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Secondary alkyllithium reagents were prepared stereoselectively via an iodo–lithium exchange by using tert-butyllithium. The resulting secondary alkyllithiums were converted directly into the corresponding alkylcopper reagents by transmetalation with copper(I) bromide–triethyl phosphite [CuBr·P(OEt)3] with retention of configuration and without significant loss of stereoselectivity. The resulting alkylcopper reagents were used for carbocupration or acylation reactions. In addition, a new intramolecular carbolithiation of secondary alkyllithium reagents possessing a remote alkyne moiety was also investigated, allowing the stereoselective production of alkylidenecylobutane derivatives with very high stereocontrol.

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3

Pereira, Ana Margarida, Honorina Cidade, and Maria Elizabeth Tiritan. "Stereoselective Synthesis of Flavonoids: A Brief Overview." Molecules 28, no. 1 (January 3, 2023): 426. http://dx.doi.org/10.3390/molecules28010426.

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Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented. Those approaches encompass stereoselective chalcone epoxidation, Sharpless asymmetric dihydroxylation, Mitsunobu reaction, and the cycloaddition of 1,4-benzoquinone. Chiral auxiliaries, organo-, organometallic, and biocatalysis, as well as the chiral pool approach were also employed with the goal of obtaining chiral bioactive flavonoids with a high enantiomeric ratio. Additionally, the employment of the Diels–Alder reaction based on the stereodivergent reaction on a racemic mixture strategy or using catalyst complexes to synthesise pure enantiomers of flavonoids was reported. Furthermore, biomimetic pathways displayed another approach as illustrated by the asymmetric coupling of 2-hydroxychalcones driven by visible light. Recently, an asymmetric transfer hydrogen-dynamic kinetic resolution was also applied to synthesise (R,R)-cis-alcohols which, in turn, would be used as building blocks for the stereoselective synthesis of flavonoids.

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4

Soorukram, Darunee, Manat Pohmakotr, Chutima Kuhakarn, and Vichai Reutrakul. "Stereoselective Synthesis of Tetrahydrofuran Lignans." Synthesis 50, no. 24 (October 2, 2018): 4746–64. http://dx.doi.org/10.1055/s-0037-1610289.

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This short review aims to summarize the reports on stereoselective synthesis of naturally occurring tetrahydrofuran lignans published during the period of 2006 to 2018. The stereoselective construction of non-natural tetrahydrofuran frameworks is not included in this review.1 Introduction2 Stereoselective Synthesis of 2,5-Diaryltetrahydrofuran (CL5-a)2.1 Synthesis of CL5-a via Friedel–Crafts Arylation or Nucleophilic Addition/Reduction of γ-Butyrolactones2.2 Synthesis of CL5-a via Intramolecular Cyclization of 1,4-Diarylbutanediols2.3 Synthesis of CL5-a via Diastereoselective Hydrogenation of Furan Derivatives2.4 Synthesis of CL5-a via Cycloaddition Reaction of Substituted Cyclopropane Derivatives3 Stereoselective Synthesis of 2-Aryl-4-benzyltetrahydrofuran (CL5-b)4 Stereoselective Synthesis of 3,4-Dibenzyltetrahydrofuran (CL5-c)5 Conclusions

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5

Uwamori, Masahiro, and Masahisa Nakada. "Collective Total Synthesis of PPAPs: Total Synthesis of Clusianone via Intramolecular Cyclopropanation." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800721.

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The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence which has been utilized for the total syntheses of nemorosone garsubellin A and hyperforin: intramolecular cyclopropanation formation of a geminal dimethyl group and regioselective ring opening of cyclopropane. Further elaboration including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains was employed to complete the total synthesis of clusianone.

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6

Klegraf, Ellen, and Horst Kunz. "Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives." Zeitschrift für Naturforschung B 67, no. 4 (April 1, 2012): 389–405. http://dx.doi.org/10.1515/znb-2012-0413.

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The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.

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7

Darvesh, Sultan, Andrew S. Grant, David I. Magee, and Zdenek Valenta. "An approach to the synthesis of bruceantin. The synthesis of a tetracyclic intermediate." Canadian Journal of Chemistry 67, no. 12 (December 1, 1989): 2237–40. http://dx.doi.org/10.1139/v89-348.

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An intermediate (20) containing four of the five rings and seven of the ten chiral centers of bruceantin (1) was prepared. In a key reaction, 3-iodo-1-trimethylsilyl-5-hexen-1-yne (9) was found to add chemoselectively and stereoselectively to a dianion. The sequence also includes a selective attack by a sulfinate (17) on the terminal acetylene C-atom of the dianion of a keto acetylene, a concomitant cyclization in which the acetylene acts as an electrophile, and the use of the resulting allyl sulfoxide for the introduction of oxygen functionality by a reductive rearrangement. Keywords: bruceantin, sigmatropic rearrangement, stereoselective alkylation.

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8

Kobayashi, S. "Stereoselective Synthesis." Synthesis 1995, no. 07 (July 1995): 878. http://dx.doi.org/10.1055/s-1995-3988.

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9

Hanson, J. R. "Stereoselective synthesis." Journal of Organometallic Chemistry 525, no. 1-2 (November 1996): 303–4. http://dx.doi.org/10.1016/s0022-328x(96)06459-5.

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10

Chaloner, Penny A. "Stereoselective synthesis." Journal of Organometallic Chemistry 331, no. 2 (September 1987): C18—C19. http://dx.doi.org/10.1016/0022-328x(87)80032-3.

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11

Cannon, Joseph G. "Stereoselective Synthesis." Journal of Pharmaceutical Sciences 76, no. 7 (July 1987): 582. http://dx.doi.org/10.1002/jps.2600760720.

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12

Misra, Anup Kumar, Arin Gucchait, and Monalisa Kundu. "Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose." Synthesis 53, no. 19 (June 24, 2021): 3613–20. http://dx.doi.org/10.1055/s-0037-1610777.

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AbstractA pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective glycosylation reaction. Functionalized monosaccharide intermediates were prepared judiciously and stereoselectively assembled to get the desired pentasaccharide derivative in excellent yield.

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13

Ramanujan, Vyasabhattar, Shaik Sadikha, and Kumar Pavan. "Stereoselective synthesis of (-)-tetrahydropyrenophorol." Journal of the Serbian Chemical Society 85, no. 9 (2020): 1129–36. http://dx.doi.org/10.2298/jsc190823040r.

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Tetrahydropyrenophorol, an interesting macrodiolide, was isolated from the plant Fagonia cretica. The total synthesis of (?)-1-tetrahydropyrenophorol was achieved in an elegant and linear manner from readily an accessible racemic epoxide. The archetypal reactions include regioselective opening of the epoxide, Sharpless asymmetric dihydroxylation, and Mitsunobu cyclodimerization to construct the requisite 16-membered bis-lactone. The synthetic approach demonstrated here is very simple and could be used for the syntheses of related compounds in an economic and highly stereoselective way.

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14

Zakia Afzal, Zakia Afzal, and Naghmana Rashid and Humaira Nadeem Naghmana Rashid and Humaira Nadeem. "Stereoselective Synthesis, Spectral Characterization, Docking and Biological Screening of Coumarin Derivatives." Journal of the chemical society of pakistan 43, no. 3 (2021): 330. http://dx.doi.org/10.52568/000580/jcsp/43.03.2021.

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The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%. The synthesized compounds were characterized by UV, IR, 1H NMR, 13C NMR, EIMS, UVCD, VCD and Chiral HPLC. The major focus of this research was to develop anticoagulant compounds and therefore the molecular docking studies were carried out with crystal structure of vitamin k epoxide reductase (3kp9) and then screened for in-vitro anticoagulant activity by using warfarin as positive control. Out of six synthesized compounds, four compounds (1,2,5,6) have shown greater binding affinity with 3kp9 than warfarin. In in-vitro anticoagulant studies, all compounds showed improved IC50 values than warfarin. Besides anticoagulant activity, antimocrobial activities were also carried out with six different strains of bacteria and fungi. Compound (5) showed 79% inhibition against Bacillus subtillis and 62 % inhibition against Staphylococcus aureus.

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15

Zakia Afzal, Zakia Afzal, and Naghmana Rashid and Humaira Nadeem Naghmana Rashid and Humaira Nadeem. "Stereoselective Synthesis, Spectral Characterization, Docking and Biological Screening of Coumarin Derivatives." Journal of the chemical society of pakistan 43, no. 3 (2021): 330. http://dx.doi.org/10.52568/000580.

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The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%. The synthesized compounds were characterized by UV, IR, 1H NMR, 13C NMR, EIMS, UVCD, VCD and Chiral HPLC. The major focus of this research was to develop anticoagulant compounds and therefore the molecular docking studies were carried out with crystal structure of vitamin k epoxide reductase (3kp9) and then screened for in-vitro anticoagulant activity by using warfarin as positive control. Out of six synthesized compounds, four compounds (1,2,5,6) have shown greater binding affinity with 3kp9 than warfarin. In in-vitro anticoagulant studies, all compounds showed improved IC50 values than warfarin. Besides anticoagulant activity, antimocrobial activities were also carried out with six different strains of bacteria and fungi. Compound (5) showed 79% inhibition against Bacillus subtillis and 62 % inhibition against Staphylococcus aureus.

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16

Tobrman, Tomáš, and Sergej Mrkobrada. "Palladium-Catalyzed Cross-Coupling Reactions of Borylated Alkenes for the Stereoselective Synthesis of Tetrasubstituted Double Bond." Organics 3, no. 3 (July 20, 2022): 210–39. http://dx.doi.org/10.3390/org3030017.

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The stereoselective formation of tetrasubstituted alkenes remains one of the key goals of modern organic synthesis. In addition to other methods, the stereoselective synthesis of tetrasubstituted alkenes can be achieved by means of cross-coupling reactions of electrophilic and nucleophilic alkene templates. The use of electrophilic templates for the stereoselective synthesis of tetrasubstituted alkenes has previously been described. Therefore, the present review summarizes the procedures available for the stereoselective preparation of tetrasubstituted alkenes using stable and isolable nucleophilic templates.

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17

Picoul, W., O. Bedel, A. Haudrechy, and Y. Langlois. "Progress in fumagillin synthesis." Pure and Applied Chemistry 75, no. 2-3 (January 1, 2003): 235–49. http://dx.doi.org/10.1351/pac200375020235.

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After a brief account of the syntheses previously described in literature, several approaches of the antiangiogenic sesquiterpene fumagillin are described. Particularly, a Claisen–Ireland ring-closing metathesis strategy allowed the stereoselective preparation of several advanced intermediates in the fumagillin synthesis.

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18

Miller, David, François Bilodeau, and Robert H. Burnell. "Stereoselective syntheses of isomers of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa blotch leafminer (Agromyza frontella (Rondani))." Canadian Journal of Chemistry 69, no. 7 (July 1, 1991): 1100–1106. http://dx.doi.org/10.1139/v91-163.

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Two related stereoselective syntheses of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa leafminer, are described to show that pulegone can serve as a useful starting material for the preparation of chiral aliphatic isoprenoid compounds. The schemes are designed to place the stereogenic center of pulegone at C.3 in one synthesis and at C.7 in the other so that the optical properties of the products can be compared with one another and with the values calculated using Brewster's rules. Key words: chiral hydrocarbons, stereoselective synthesis, pheromone, Agromyza frontella.

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19

Serra, Stefano, Alessandra A. Cominetti, and Veronica Lissoni. "Use of (S)-trans-γ-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products." Natural Product Communications 9, no. 3 (March 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900312.

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A comprehensive study of the exploitation of ( S)- trans-γ-monocyclofarnesol as a useful chiral building block for the stereoselective synthesis of natural diterpene derivatives is here described. The farnesol derivative (+)-1 was used as starting material in the preparation of the diterpenes ( S)-dehydroambliol-A and ( S)-trixagol, as well as for the syntheses of the dinorditerpene ( S)-dinortrixagone and of the guanidine-interrupted terpenoid ( S)-dotofide. Key steps of the presented syntheses were the cross-coupling between an allyl acetate and a Grignard reagent, the Wittig reaction, the selective preparation of a diacylguanidine derivative and the alkylation of a sulfone derivative, followed by the reductive removal of the same functional group. It is worth noting that the natural products (+)-8, (+)-12 and (+)-15 were prepared stereoselectively for the first time, thus allowing the unambiguous assignment of their absolute configuration.

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20

Sefkow, M., M. Raschke, and C. Steiner. "Enantioselective synthesis and biological evaluation of a-hydroxylated lactone lignans." Pure and Applied Chemistry 75, no. 2-3 (January 1, 2003): 273–78. http://dx.doi.org/10.1351/pac200375020273.

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A short and efficient synthesis of enantiomerically pure α-hydroxylated lactone lignans starting from commercially available diisopropyl malate is presented. Stereoselective alkylation with various benzyl bromides and saponification yielded the corresponding succinic acids. Acetalization afforded the dioxolanones, which were stereoselectively alkylated. Reduction (and deprotection, where required) yielded the lactone lignans in up to 30 % overall yield. The inhibition of the proliferation of HT29 colon cancer cells was investigated. One lignane, bis-2,4,6 trimethylbenzyllactone lignan, was active (IC50 = 35 μM), whereas all other tested lignans were inactive within the investigated concentration range.

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21

Joyeux, Benjamin, Antoine Gamet, Nicolas Casaretto, and Bastien Nay. "Asymmetric synthesis of a stereopentade fragment toward latrunculins." Beilstein Journal of Organic Chemistry 19 (April 3, 2023): 428–33. http://dx.doi.org/10.3762/bjoc.19.32.

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Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target similar disconnections, especially an aldol strategy involving a recurrent 4-acetyl-1,3-thiazolidin-2-one ketone partner. Herein, we describe an alternative disconnection and subsequent stereoselective transformations to construct a stereopentade amenable to latrunculin and analogue synthesis, starting from (+)-β-citronellene. Key stereoselective transformations involve an asymmetric Krische allylation, an aldol reaction under 1,5-anti stereocontrol, and a Tishchenko–Evans reduction accompanied by a peculiar ester transposition, allowing to install key stereogenic centers of the natural products.

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22

Shukla, Vilas B., and Pushpa R. Kulkarni. "Production of allyl phenyl carbinol (APC) by biotrans-formation using Rhizopus arrhizus." Brazilian Archives of Biology and Technology 43, no. 3 (2000): 249–52. http://dx.doi.org/10.1590/s1516-89132000000300001.

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The objective of the present work was to study the stereoselective synthesis of homo-allylic alcohol using stereoselective hydrolysis by Rhizopus arrhizus and also to study the stereoselective synthesis of allyl phenyl carbinol (APC) or 1-Phenyl-3-butene-1-o by combination of chemical synthesis and biotransformation from cheap raw materials such as benzaldehyde and allyl bromide. Stereospecific synthesis of allyl phenyl carbinol (APC) was achieved by acetate hydrolysis by R. arrhizus giving R (+) enantiomer. Maximum enantiomeric excess of APC was obtained at 16 h where as maximum yield of it was obtained at 48 h of biotransformation.

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23

Vetica, Fabrizio, Fabiana Pandolfi, Luca Pettazzoni, Francesca Leonelli, and Martina Bortolami. "Organocatalyst Design for the Stereoselective Annulation towards Bicyclic Diketones and Analogues." Symmetry 14, no. 2 (February 10, 2022): 355. http://dx.doi.org/10.3390/sym14020355.

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The Wieland–Miescher ketone, Hajos–Parrish–Eder–Sauer–Wiechert ketone, and their analogues are bicyclic diketones essential as building blocks for the synthesis of several natural and bioactive molecules. For this reason, since 1971, when Hajos and Parrish and Eder, Sauer, and Wiechert reported the stereoselective synthesis of these compounds promoted by L-proline, numerous methodologies and organocatalysts have been studied over the years with the aim of identifying increasingly efficient asymmetrical syntheses of these bicyclic ketones. This review will outline the methodological and stereochemical features of the organocatalytic stereoselective synthesis of these bicyclic scaffolds based on the different organocatalysts employed from 1971 until today. Particular emphasis will be given to the structural features of the catalysts and to the reaction conditions.

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24

Cantin, Michel, Yao-Chang Xu, and Pierre Deslongchamps. "Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered triene macrocycle." Canadian Journal of Chemistry 68, no. 12 (December 1, 1990): 2144–52. http://dx.doi.org/10.1139/v90-329.

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The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels–Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85 °C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250 °C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yield. Keywords: stereocontrolled synthesis, macrocycle, tricyclic compound, transannular Diels–Alder reaction.

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25

Manikanta, Gembali, Galla Raju, and Palakodety Radha Krishna. "Stereoselective total synthesis of ent-hyptenolide." RSC Advances 5, no. 11 (2015): 7964–69. http://dx.doi.org/10.1039/c4ra13708f.

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26

Adhikari, Raju, Darren J. Cundy, Craig L. Francis, Mariana Gebara-Coghlan, Beata Krywult, Carolyn Lubin, Gregory W. Simpson, and Qi Yang. "A Scalable Stereoselective Synthesis of Scymnol." Australian Journal of Chemistry 58, no. 1 (2005): 34. http://dx.doi.org/10.1071/ch04175.

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A high-yielding, stereoselective synthesis of scymnol 1 has been carried out in five steps starting from commercially available cholic acid 2. The synthesis was designed with the aim of eventual large-scale processing. Triformyloxycholic acid chloride 4 was treated with the magnesium enolate of diethyl malonate to afford the β-keto diester, diethyl 3α,7α,12α-triformyloxy-24-oxo-5β-cholestane-26,27-dioate 5. The key step in the synthesis was the stereoselective hydrogenation of β-keto diester 5 to give the corresponding β-hydroxy diester 6 using a BINAP ruthenium(ii) catalyst. Subsequent reduction of the diester moiety and deprotection of the hydroxyl groups afforded scymnol 1.

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27

Naik, Siddhi D., Girish Chandra, Pramod K. Sahu, Hong-Rae Kim, Shuhao Qu, Ji-seong Yoon, and Lak Shin Jeong. "Stereo- and regio-selective synthesis of 3′-C-substituted-(N)-methanocarba adenosines as potential anticancer agents." Organic Chemistry Frontiers 3, no. 11 (2016): 1472–80. http://dx.doi.org/10.1039/c6qo00358c.

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Synthesis of 3′-C-substituted-(N)-methanocarba adenosines using stereoselective cyclopropanation, stereoselective nucleophilic addition, regioselective isopropylidene cleavage and regioselective cyclic sulfate condensation.

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28

Andersen, Marc W., Bernhard Hildebrandt, Georg Dahmann, and Reinhard W. Hoffmann. "Stereoselective Synthesis of Alcohols, XXXVIII Stereoselective Total Synthesis of the Denticulatins." Chemische Berichte 124, no. 9 (September 1991): 2127–39. http://dx.doi.org/10.1002/cber.19911240940.

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29

Hu, Xiang-Guo, and Luke Hunter. "Stereoselectively fluorinated N-heterocycles: a brief survey." Beilstein Journal of Organic Chemistry 9 (November 29, 2013): 2696–708. http://dx.doi.org/10.3762/bjoc.9.306.

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The stereoselective incorporation of fluorine atoms into N-heterocycles can lead to dramatic changes in the molecules’ physical and chemical properties. These changes can be rationally exploited for the benefit of diverse fields such as medicinal chemistry and organocatalysis. This brief review will examine some of the effects that fluorine substitution can have in N-heterocycles, including changes to the molecules’ stability, their conformational behaviour, their hydrogen bonding ability, and their basicity. Finally, some methods for the synthesis of stereoselectively fluorinated N-heterocycles will also be reviewed.

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30

Battula, S. R. K., G. V. Subbareddy, I. E. Chakravarthy, and V. Saravanan. "Stereoselective synthesis of 4-aminobenzo[c][1,2]thiazine via modification of the Harmata benzothiazine synthesis." RSC Advances 6, no. 61 (2016): 55710–14. http://dx.doi.org/10.1039/c6ra08590c.

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31

Yang, Yang. "Building polyfunctional piperidines: a stereoselective strategy of a three-component Mannich reaction inspired by biosynthesis and applications in the synthesis of natural alkaloids (+)-241D; (−)-241D; isosolenopsin A and (−)-epimyrtine." RSC Advances 5, no. 24 (2015): 18894–908. http://dx.doi.org/10.1039/c4ra14418j.

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32

Tortosa, Mariola, Víctor Martín-Heras, and Alejandro Parra. "Cyclopropyl- and Cyclobutylboronates and -silanes: A Stereoselective Approach." Synthesis 50, no. 03 (December 14, 2017): 470–84. http://dx.doi.org/10.1055/s-0036-1589133.

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Chiral cyclopropyl- and cyclobutylboronic esters and -silanes have become attractive intermediates for the preparation of functionalized small rings. This review highlights the stereoselective methods developed for their preparation, including both diastereo- and enantioselective approaches.1 Introduction2 Stereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes2.1 Diastereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes2.2 Asymmetric Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes3 Conclusions

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33

D'Onofrio, A., L. Copey, L. Jean-Gérard, C. Goux-Henry, G. Pilet, B. Andrioletti, and E. Framery. "d-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides." Organic & Biomolecular Chemistry 13, no. 34 (2015): 9029–34. http://dx.doi.org/10.1039/c5ob01323b.

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34

Hanquet, B., B. Tabyaoui, J. C. Caille, M. Farnier, and R. Guilard. "Synthèse stéréosélective de (±) boschnialactone, (±) 7-épiteucriumlactone et (±) 7-épiisoiridomyrmécine. Étude de la stéréochimie par spectroscopie de résonance magnétique nucléaire." Canadian Journal of Chemistry 68, no. 4 (April 1, 1990): 620–27. http://dx.doi.org/10.1139/v90-095.

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The stereoselective syntheses of (±) boschnialactone 1, (±) 7-epiteucriumlactone 2, and (±) 7-epiisoiridomyrmecine 3 are described. Their preparation involved Stetter's reaction followed by nucleophilic addition of lithium enolates of suitable esters. Silylated reagents are used in the lactonisation step and the observed yields are between 63 and 78%. The proposed structural analysis is not in accord with the results of a previous study. The nuclear magnetic resonance data are determined using ID and 2D proton and carbon NMR experiments. Keywords: stereoselective synthesis, boschnialactone, 7-epiteucriumlactone, 7-epiisoiridomyrmecine, 1H and 13C NMR.

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35

Penumati, Nageshwar Rao, and Nagaiah Kommu. "Stereoselective Synthesis of (+)-α-Conhydrine from R-(+)-Glyceraldehyde." Organic Chemistry International 2014 (October 20, 2014): 1–7. http://dx.doi.org/10.1155/2014/982716.

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Stereoselective synthesis of (+)-α-Conhydrine was accomplished from protected (R)-(+)-glyceraldehyde, a familiar carbohydrate predecessor. Our synthetic strategy featured the following two key reactions. One is Zn-mediated stereoselective aza-Barbier reaction of imine 6 with allyl bromide to afford chiral homoallylic amine 7, and the other is ring-closing metathesis.

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36

Kellersmann, C., W. Francke, and H. Steinhart. "Synthesis of (Z,Z)-octadeca-10,12-dienoic acid." Czech Journal of Food Sciences 22, SI - Chem. Reactions in Foods V (January 1, 2004): S73—S75. http://dx.doi.org/10.17221/10615-cjfs.

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(Z,Z)-Octadeca-10,12-dienoic acid was synthesised by coupling (Z)-1-bromohept-1-ene with protected undec-10-yne-1-ol. Stereoselective hydrogenation of the triple bond of the obtained enyne-system followed by deprotection yielded (Z,ZZ)-octadeca-10,12-dienol. The latter can be easily oxidized to the corresponding acid.

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37

Serra, Stefano. "Enzyme-Mediated Stereoselective Synthesis." Catalysts 9, no. 9 (September 11, 2019): 763. http://dx.doi.org/10.3390/catal9090763.

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38

Garcia, P., D. Diez, A. Anton, N. Garrido, I. Marcos, P. Basabe, and J. Urones. "Stereoselective Synthesis of Cyclopropanols." Mini-Reviews in Organic Chemistry 3, no. 4 (November 1, 2006): 291–314. http://dx.doi.org/10.2174/157019306778742878.

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39

Kumar, A. Shashidhar, Pushpal Bhaket, and B. Venkateswara Rao. "Stereoselective synthesis of (-)-pestalotin." Arkivoc 2005, no. 3 (November 12, 2004): 74–82. http://dx.doi.org/10.3998/ark.5550190.0006.310.

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40

Nagasaka, Tatsuo, Hiroto Yamamoto, Hideki Hayashi, Hiroki Kato, Miyako Kawaida, Kazuhiro Yamaguchi, and Fumiko Hamaguchi. "Stereoselective Synthesis of (±)-Epilupinine." HETEROCYCLES 29, no. 6 (1989): 1209. http://dx.doi.org/10.3987/com-89-4972.

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41

Shakhmaev, R. N., A. U. Ishbaeva, A. Sh Sunagatullina, and V. V. Zorin. "Stereoselective synthesis of sarmentine." Russian Journal of General Chemistry 81, no. 9 (September 2011): 1915–17. http://dx.doi.org/10.1134/s1070363211090337.

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42

Streith, J. "Book Review, Stereoselective Synthesis." Synthesis 1996, no. 12 (December 1996): 1515–16. http://dx.doi.org/10.1055/s-1996-4403.

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43

Laschat, Sabine, and Tim Dickner. "Stereoselective Synthesis of Piperidines." Synthesis 2000, no. 13 (2000): 1781–813. http://dx.doi.org/10.1055/s-2000-8218.

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44

Breinbauer, Rolf. "Classics in Stereoselective Synthesis." Synthesis 2009, no. 10 (May 2009): 1760. http://dx.doi.org/10.1055/s-0029-1216803.

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45

Murga, Juan, Eva Falomir, Jorge García-Fortanet, Miguel Carda, and J. Alberto Marco. "Stereoselective Synthesis of Microcarpalide." Organic Letters 4, no. 20 (October 2002): 3447–49. http://dx.doi.org/10.1021/ol0265463.

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46

Jakobsen, Martin Gjerde, Anders Vik, and Trond Vidar Hansen. "Stereoselective synthesis of zooxanthellactone." Tetrahedron Letters 55, no. 17 (April 2014): 2842–44. http://dx.doi.org/10.1016/j.tetlet.2014.03.085.

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47

Ho, Tse-Lok, and Qi-xian Lin. "Stereoselective synthesis of (±)-tacamonine." Tetrahedron 64, no. 45 (November 2008): 10401–5. http://dx.doi.org/10.1016/j.tet.2008.08.049.

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48

Nagasaka, Tatsuo, and Yuji Koseki. "Stereoselective Synthesis of Tilivalline1." Journal of Organic Chemistry 63, no. 20 (October 1998): 6797–801. http://dx.doi.org/10.1021/jo972158g.

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49

Canoa, Pilar, Nuria Vega, Manuel Pérez, Generosa Gómez, and Yagamare Fall. "Stereoselective synthesis of polytetrahydropyrans." Tetrahedron Letters 49, no. 7 (February 2008): 1149–51. http://dx.doi.org/10.1016/j.tetlet.2007.12.053.

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50

Falomir, Eva, Juan Murga, Miguel Carda, and J. Alberto Marco. "Stereoselective synthesis of spicigerolide." Tetrahedron Letters 44, no. 3 (January 2003): 539–41. http://dx.doi.org/10.1016/s0040-4039(02)02588-1.

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