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Journal articles on the topic 'Diastereoselective'

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Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Pereira, Vera L. P., Francine P. Meirelis, and Bruna G. N. Vieira. "Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans-α,β-Disubstituted γ-Lactams from (S)-N,N-Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions." Synthesis 52, no. 23 (August 24, 2020): 3650–56. http://dx.doi.org/10.1055/s-0040-1706423.

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γ-Monosubstituted and trans-α,β-disubstituted γ-lactams were diastereoselectively synthesized from common intermediates (S)-N,N-dibenzylated aldehydes derived from natural l-(α)-amino acids, employing a divergent approach. The key features of the routes include diastereoselective Henry and Michael reactions that produced chiral γ-nitroester derivatives, which were subsequently submitted to a tandem reduction-lactamization sequence providing the title compounds. The versatility of routes can allow the preparation of several other mono-, di-, or tri-substituted γ-lactams.

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2

Canonne, Perséphone, Raynald Boulanger, and Michel Bernatchez. "Diastereoselective spiroannelation." Tetrahedron Letters 28, no. 42 (January 1987): 4997–5000. http://dx.doi.org/10.1016/s0040-4039(00)96679-6.

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3

Jung, Young, Seung Kim, Yeon Hong, Sook Park, Kyung Kang, So Kim, Jung Park, and In Kim. "Divergent Synthesis of Aminocyclopentitol Analogues via Stereoselective Amination of Cyclic Polybenzyl Ether with Chlorosulfonyl Isocyanate." Synlett 26, no. 08 (February 20, 2015): 1089–92. http://dx.doi.org/10.1055/s-0034-1380227.

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The divergent synthesis of some novel aminocyclopentitol analogues was concisely achieved from readily available d-galactose via the highly diastereoselective amination of carbocyclic polybenzyl ether using chlorosulfonyl isocyanate, diastereoselective dihydroxylation, and epoxidation as the key steps.

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4

Chevis, Philip J., Sirilak Wangngae, Thanaphat Thaima, Anthony W. Carroll, Anthony C. Willis, Mookda Pattarawarapan, and Stephen G. Pyne. "Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines." Chemical Communications 55, no. 43 (2019): 6050–53. http://dx.doi.org/10.1039/c9cc02765c.

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A highly diastereoselective synthesis (dr = 99 : 1 97 : 3) of enantioenriched anti-α-allyl-β-fluoroamines (ee = 86–92%) has been developed involving a highly diastereoselective Petasis allyl borono-Mannich reaction of (S)- or (R)-α-fluoroaldehydes.

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5

Ramaswamy, Sowmianarayanan, and Allan C. Oehlschlager. "Efficient synthesis of exo- and endo-brevicomin from a single precursor." Canadian Journal of Chemistry 67, no. 5 (May 1, 1989): 794–96. http://dx.doi.org/10.1139/v89-120.

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Diastereoselective reduction of 2-propionyl-6-methyl-3,4-dihydropyran and its ring opened derivatives, followed by acidic work-up, gives mixtures rich (>9:1) of either exo- or endo-brevicomin. Keywords: exo- and endo-brevicomin, diastereoselective ketone reduction.

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6

Li, Chunbao, Wenjiao Yuan, and Yali Liu. "A Rapid and Diastereoselective Synthesis of 2-Deoxy-2-iodo-α-glycosides and its Mechanism for Diastereoselectivity." Synlett 28, no. 15 (May 24, 2017): 1975–78. http://dx.doi.org/10.1055/s-0036-1588440.

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Reductive deiodination of 2-deoxy-2-iodo-glycoside is an efficient and practical approach for the synthesis of 2-deoxyglycosides, which are moieties of bioactive compounds. However, inseparable diastereoisomers are usually formed in the preparation of 2-deoxy-2-iodo-glycosides via glycosylation of glycals with alcohols using current methods. To overcome this problem, a rapid and diastereoselective transformation of glycals and alcohols into 2-deoxy-2-iodo-α-glycosides enabled by I2/PhI(OAc)2 has been developed. 14 glycals, derived from 13 monosaccharides and one disaccharide, diastereoselectively yielded α-glycosides. Only in two cases the diastereoselectivity of the glycosylation was poor. The yields of glycosylation range from 73% to 95%, and the reactions are finished in only five minutes. Investigations for better diastereoselectivity by comparing I2/Ph(OAc)2- with I2/Cu(OAc)2-mediated glycosylations using UV analysis have been conducted.

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7

Achard, Thierry J. R., Yuri N. Belokon’, Jamie Hunt, Michael North, and Francesca Pizzato. "Diastereoselective Darzens condensations." Tetrahedron Letters 48, no. 17 (April 2007): 2961–64. http://dx.doi.org/10.1016/j.tetlet.2007.03.010.

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8

Taber, Douglass F., Yanong Wang, and Thomas F. Pahutski. "Diastereoselective Cyclopentane Construction." Journal of Organic Chemistry 65, no. 12 (June 2000): 3861–63. http://dx.doi.org/10.1021/jo991866u.

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9

Spanu, Pietro, Gloria Rassu, Luigi Pinna, Lucia Battistini, and Giovanni Casiraghi. "Diastereoselective synthesis of." Tetrahedron: Asymmetry 8, no. 19 (October 1997): 3237–43. http://dx.doi.org/10.1016/s0957-4166(97)00431-x.

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10

Sandin, Peter, Francesca Baldelli Bombelli, Benedetta Castroflorio, Christoph Müller, Jürgen Obermeier, Göran Karlsson, Katarina Edwards, Piero Baglioni, and Debora Berti. "Diastereoselective self-assembly of clofarabine lipids." New J. Chem. 38, no. 11 (2014): 5247–53. http://dx.doi.org/10.1039/c4nj00856a.

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11

Ievlev, Mikhail Yu, Oleg V. Ershov, Mikhail Yu Belikov, Angelina G. Milovidova, Viktor A. Tafeenko, and Oleg E. Nasakin. "Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group." Beilstein Journal of Organic Chemistry 12 (September 27, 2016): 2093–98. http://dx.doi.org/10.3762/bjoc.12.198.

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An efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.

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12

Kumar, Amit, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, and Erik V. Van der Eycken. "Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines." Beilstein Journal of Organic Chemistry 9 (October 14, 2013): 2097–102. http://dx.doi.org/10.3762/bjoc.9.246.

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An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.

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13

Cativiela, Carlos, Maria Dolores Diaz-De-Villegas, and José Antonio Galvez. "Chiral 2-acetamidoacrylates in conjugate addition – asymmetric enolate trapping reactions. Asymmetric synthesis of phenylalanine." Canadian Journal of Chemistry 70, no. 9 (September 1, 1992): 2325–28. http://dx.doi.org/10.1139/v92-294.

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A new route to the asymmetric synthesis of α-amino acids based on the reactivity of chiral 2-acetamidoacrylates with nucleophiles through a conjugate addition followed by diastereoselective protonation of the enolate is described. Phenylalanine precursors are obtained in excellent chemical yields (80–95%) with moderate diastereomeric excess (0–44%) through the reaction of chiral 2-acetamidoacrylates with phenylmagnesium bromide in the presence of CuI followed by diastereoselective enolate protonation.

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14

Ashitha, Kizhakkan Thiruthi, Puthiya Purayil Vinaya, Ajay Krishna, Deepthy Cheeran Vincent, Renjitha Jalaja, Sunil Varughese, and Sasidhar Balappa Somappa. "I2/TBHP mediated diastereoselective synthesis of spiroaziridines." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1588–93. http://dx.doi.org/10.1039/c9ob02711d.

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15

Cogswell, Thomas J., Craig S. Donald, De-Liang Long, and Rodolfo Marquez. "Short and efficient synthesis of fluorinated δ-lactams." Organic & Biomolecular Chemistry 13, no. 3 (2015): 717–28. http://dx.doi.org/10.1039/c4ob01547a.

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16

Csuk, René, Martina Schaade, and Andrea Schmidt. "Diastereoselective dimerization of aldonolactones." Tetrahedron 50, no. 41 (January 1994): 11885–92. http://dx.doi.org/10.1016/s0040-4020(01)89302-9.

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17

Miller, Scott J., and Christopher D. Bayne. "Diastereoselective Enolsilane Coupling Reactions." Journal of Organic Chemistry 62, no. 17 (August 1997): 5680–81. http://dx.doi.org/10.1021/jo971050y.

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18

Adamo, M., D. Donati, E. Duffy, and P. Sarti-Fantoni. "Diastereoselective Synthesis of Spiroisoxazolines." Synfacts 2006, no. 01 (December 16, 2005): 0031. http://dx.doi.org/10.1055/s-2005-921707.

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19

Cossy, Janine, Nicolas Blanchard, Céline Hamel, and Christophe Meyer. "Diastereoselective Hydroboration of Isopropenylcyclopropanes." Journal of Organic Chemistry 64, no. 8 (April 1999): 2608–9. http://dx.doi.org/10.1021/jo990001d.

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20

Fox, J., Z. Yang, and X. Xie. "Diastereoselective Synthesis of Methylenecyclopropanes." Synfacts 2006, no. 8 (August 2006): 0812. http://dx.doi.org/10.1055/s-2006-941949.

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21

Panda, Siva, C. Hall, Oleksandr Detistov, Peter Steel, Abdullah Asiri, and Alan Katritzky. "Diastereoselective Synthesis of Methanopyridoxazocinones." Synlett 25, no. 18 (October 7, 2014): 2654–60. http://dx.doi.org/10.1055/s-0034-1379182.

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22

Böhrsch, Verena, Jürgen Neidhöfer, and Siegfried Blechert. "Diastereoselective Ring-Rearrangement Metathesis." Angewandte Chemie International Edition 45, no. 8 (February 13, 2006): 1302–5. http://dx.doi.org/10.1002/anie.200503321.

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23

DUHAMEL, P. "ChemInform Abstract: Diastereoselective Halogenations." ChemInform 28, no. 12 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199712301.

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24

Neuhaus, William C., and Marisa C. Kozlowski. "Diastereoselective Synthesis of Benzoxanthenones." Chemistry – An Asian Journal 15, no. 7 (April 2020): 1039–43. http://dx.doi.org/10.1002/asia.201901727.

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25

Tredwell, Matthew, Jennifer A R. Luft, Marie Schuler, Kenny Tenza, Kendall N Houk, and Véronique Gouverneur. "Fluorine-Directed Diastereoselective Iodocyclizations." Angewandte Chemie 120, no. 2 (January 2008): 363–66. http://dx.doi.org/10.1002/ange.200703465.

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26

Muncipinto, Giovanni, Philip N. Moquist, Stuart L. Schreiber, and Scott E. Schaus. "Catalytic Diastereoselective Petasis Reactions." Angewandte Chemie 123, no. 35 (July 12, 2011): 8322–25. http://dx.doi.org/10.1002/ange.201103271.

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27

Tredwell, Matthew, Jennifer A R. Luft, Marie Schuler, Kenny Tenza, Kendall N Houk, and Véronique Gouverneur. "Fluorine-Directed Diastereoselective Iodocyclizations." Angewandte Chemie International Edition 47, no. 2 (January 2008): 357–60. http://dx.doi.org/10.1002/anie.200703465.

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28

Kumar, Chepuri V. Suneel, Caleb W. Holyoke, and Fraser F. Fleming. "Diastereoselective Electrophile-Directed Alkylations." European Journal of Organic Chemistry 2019, no. 11 (March 3, 2019): 2093–106. http://dx.doi.org/10.1002/ejoc.201900174.

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29

Muncipinto, Giovanni, Philip N. Moquist, Stuart L. Schreiber, and Scott E. Schaus. "Catalytic Diastereoselective Petasis Reactions." Angewandte Chemie International Edition 50, no. 35 (July 12, 2011): 8172–75. http://dx.doi.org/10.1002/anie.201103271.

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30

De Kimpe, N., B. Denolf, S. Mangelinckx, and K. Törnroos. "Diastereoselective Synthesis of Cyclopropylamines." Synfacts 2007, no. 7 (July 2007): 0739. http://dx.doi.org/10.1055/s-2007-968612.

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31

Seiler, Martin, Andreas Schumacher, Ute Lindemann, Frédérique Barbosa, and Bernd Giese. "Diastereoselective Photocyclization to Dihydroindolinols." Synlett 1999, no. 10 (December 31, 1999): 1588–90. http://dx.doi.org/10.1055/s-1999-2902.

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32

Fleming, Fraser F., Subrahmanyam Gudipati, Zhiyu Zhang, Wang Liu, and Omar W. Steward. "Cyclic Nitriles: Diastereoselective Alkylations." Journal of Organic Chemistry 70, no. 10 (May 2005): 3845–49. http://dx.doi.org/10.1021/jo0501184.

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33

Braun, M., H. Sacha, D. Galle, and S. Baskaran. "Diastereoselective reactions of enolates." Pure and Applied Chemistry 68, no. 3 (January 1, 1996): 561–64. http://dx.doi.org/10.1351/pac199668030561.

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34

Müslehiddinoğlu, J., J. Li, S. Tummala, and R. Deshpande. "Diastereoselective Hydrogenation of Imines." Synfacts 2010, no. 10 (September 22, 2010): 1148. http://dx.doi.org/10.1055/s-0030-1258644.

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35

Müslehiddino′glu, J., J. Li, S. Tummala, and R. Deshpande. "Diastereoselective Hydrogenation of Imines." Synfacts 2010, no. 11 (October 21, 2010): 1326. http://dx.doi.org/10.1055/s-0030-1258838.

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36

Pyne, Stephen G. "Diastereoselective Reactions of Sulfoximines." Sulfur reports 12, no. 1 (July 1992): 57–89. http://dx.doi.org/10.1080/01961779208048778.

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37

Theberge, Cory R., and Charles K. Zercher. "Diastereoselective synthesis of bicyclopropanes." Tetrahedron Letters 35, no. 49 (December 1994): 9181–84. http://dx.doi.org/10.1016/0040-4039(94)88459-5.

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38

Bower, Justin F., and Jonathan Mj Williams. "Diastereoselective oxidation of arylsulfides." Tetrahedron Letters 35, no. 38 (September 1994): 7111–14. http://dx.doi.org/10.1016/0040-4039(94)88239-8.

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39

Salom-Roig, Xavier, and Claude Bauder. "Recent Applications in the Use of Sulfoxides as Chiral Auxiliaries for the Asymmetric Synthesis of Natural and Biologically Active Products." Synthesis 52, no. 07 (January 27, 2020): 964–78. http://dx.doi.org/10.1055/s-0039-1690803.

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The contribution of chiral sulfoxides as versatile auxiliaries in the field of organic chemistry has shown a prevalent interest in the asymmetric synthesis of natural products during the last 45 years. In this short review, we report the recent applications of these chiral auxiliaries to the synthesis of natural and biological active products highlighted from 2010 to 2019. We hope to allow the reader to have an overview of the potential of sulfoxide chemistry in the field of enantioselective synthesis.1 Introduction2 Diastereoselective Additions to Ketones2.1 Reduction of β-Keto Sulfoxides2.2 Reduction of β-Keto Sulfoxides Followed by Bromohydrin Forma tion3 Synthesis of an α-Amino α′-Sulfinyl Ketone Followed by Diastere oselective Reduction of the β-Keto Sulfoxide4 Diastereoselective Addition of Carbanionic Chiral Sulfoxides4.1 Addition to an Aldehyde4.1.1 Aldol Reactions4.1.2 Reformatsky-Type Reactions4.2 Additions to Chiral Sulfinimines5 Diastereoselective Cyclization Reactions Directed by a Chiral Sulf oxide5.1 1,4-Radical Additions5.2 Intramolecular Conjugate Additions5.3 Nazarov Cyclizations5.4 Diels–Alder Reactions6 Atropodiastereoselective Synthesis7 Conclusion

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40

Larin, Egor M., Joachim Loup, Iuliia Polishchuk, Rachel J. Ross, Andrew Whyte, and Mark Lautens. "Enantio- and diastereoselective conjugate borylation/Mannich cyclization." Chemical Science 11, no. 22 (2020): 5716–23. http://dx.doi.org/10.1039/d0sc02421j.

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Copper-catalyzed enantio- and diastereoselective conjugate borylation across Michael acceptors, with subsequent Mannich-type cyclization, was utilized to construct tetrahydroquinoline scaffolds containing three contiguous stereocenters.

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41

Pinheiro, Danielle L. J., Gabriel M. F. Batista, Pedro P. de Castro, Leonã S. Flores, Gustavo F. S. Andrade, and Giovanni W. Amarante. "A Brønsted base-promoted diastereoselective dimerization of azlactones." Beilstein Journal of Organic Chemistry 13 (December 13, 2017): 2663–70. http://dx.doi.org/10.3762/bjoc.13.264.

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A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using 1H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.

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42

Herbert, Simon A., Laura J. van Laeren, Dominic C. Castell, and Gareth E. Arnott. "Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space." Beilstein Journal of Organic Chemistry 10 (November 25, 2014): 2751–55. http://dx.doi.org/10.3762/bjoc.10.291.

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The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds.

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43

Wilkie, Ross P., Andrew R. Neal, Craig A. Johnston, Nicholas Voute, Christopher S. Lancefield, Matthew D. Stell, Federico Medda, et al. "Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction." Chemical Communications 52, no. 71 (2016): 10747–50. http://dx.doi.org/10.1039/c6cc05747k.

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44

Dong, Changming, Tianjiao Qiao, Yi Xie, Xiao Zhang, Junli Ao, and Guangxin Liang. "Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy." Organic Chemistry Frontiers 7, no. 14 (2020): 1890–94. http://dx.doi.org/10.1039/d0qo00576b.

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45

Wang, Xiaoji, Yunhao Luo, Shuanglin Qin, Yue Sun, Ning Wang, Jun Yan, and Guang Yang. "Rh-Catalyzed diastereo- and linear-selective α-allylation of chiral cycloenamines." Organic Chemistry Frontiers 7, no. 22 (2020): 3715–19. http://dx.doi.org/10.1039/d0qo01087a.

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46

Verkade, Jorge M. M., Peter J. L. M. Quaedflieg, Gerard K. M. Verzijl, Laurent Lefort, Floris L. van Delft, Johannes G. de Vries, and Floris P. J. T. Rutjes. "Enantio- and diastereoselective synthesis of γ-amino alcohols." Chemical Communications 51, no. 77 (2015): 14462–64. http://dx.doi.org/10.1039/c5cc04445f.

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47

MaGee, David I., Tammy Mallais, and George M. Strunz. "Asymmetric formal synthesis of ()-cryptosporiopsin, a metabolite of Phialophora asterris, and its 3-deschloro congener." Canadian Journal of Chemistry 82, no. 12 (December 1, 2004): 1686–91. http://dx.doi.org/10.1139/v04-145.

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An asymmetric formal synthesis of the fungal metabolites ()-cryptosporiopsin and ()-3-deschloro crypto sporiopsin has been accomplished. The asymmetry was introduced via a diastereoselective [2+2]-cycloaddition between an enoxy-ester, bearing a bulky chiral auxiliary, and dichloroketene. Diastereomeric ratios of 10:1 were obtained from the reaction mixture, but this could be increased by simple crystallization. Completion of the synthesis was only accomplished after the serendipitous discovery of a base-catalyzed rearrangement to furnish the requisite 3-chloroenone moiety.Key words: diastereoselective [2+2]-cycloaddition, rearrangement, chiral auxiliary.

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48

Donslund, Bjarke S., Nicolaj Inunnguaq Jessen, Joakim Bøgelund Jakobsen, Alicia Monleón, Rune Pagh Nielsen, and Karl Anker Jørgensen. "Enantioselective formation of cyclopropane spiroindenes from benzofulvenes by phase transfer catalysis." Chemical Communications 52, no. 84 (2016): 12474–77. http://dx.doi.org/10.1039/c6cc07170h.

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49

Feng, Ze-Nan, Jin-Yun Luo, Yang Zhang, Guang-Fen Du, and Lin He. "N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael–Michael (aldol) cascade reactions." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4700–4704. http://dx.doi.org/10.1039/c9ob00210c.

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50

Guan, Xiao-Yu, Min Tang, Zhang-Qin Liu, and WenHao Hu. "A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides." Chemical Communications 55, no. 66 (2019): 9809–12. http://dx.doi.org/10.1039/c9cc04890a.

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