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Journal articles on the topic 'Asymmetric dihydroxylation'

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Published: 4 June 2021

Last updated: 20 February 2023

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1

Kolb, Hartmuth C., Michael S. VanNieuwenhze, and K. Barry Sharpless. "Catalytic Asymmetric Dihydroxylation." Chemical Reviews 94, no. 8 (December 1994): 2483–547. http://dx.doi.org/10.1021/cr00032a009.

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2

Crispino, Gerard A., and K. Barry Sharpless. "Asymmetric dihydroxylation of squalene." Tetrahedron Letters 33, no. 30 (July 1992): 4273–74. http://dx.doi.org/10.1016/s0040-4039(00)74236-5.

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3

Jeong, Kyu-Sung, Peter Sjö, and K. Barry Sharpless. "Asymmetric dihydroxylation of enynes." Tetrahedron Letters 33, no. 27 (June 1992): 3833–36. http://dx.doi.org/10.1016/s0040-4039(00)74797-6.

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4

Fleming, Steven A., Sean M. Carroll, Jennifer Hirschi, Renmao Liu, J. Lee Pace, and J. Ty Redd. "Asymmetric dihydroxylation of allenes." Tetrahedron Letters 45, no. 17 (April 2004): 3341–43. http://dx.doi.org/10.1016/j.tetlet.2004.03.037.

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5

Kolb, Hartmuth C., and K. Barry Sharpless. "ChemInform Abstract: Asymmetric Dihydroxylation." ChemInform 30, no. 12 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199912312.

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6

Devi, Runjun, and Sajal Kumar Das. "Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates." Beilstein Journal of Organic Chemistry 13 (March 21, 2017): 571–78. http://dx.doi.org/10.3762/bjoc.13.56.

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While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxiran-2-yl)chroman, which have been used as late-stage intermediates for the asymmetric synthesis of the antihypertensive drug (S,R,R,R)-nebivolol. Noteworthy is that a large number of racemic and asymmetric syntheses of nebivolol and their intermediates have been described in the literature, however, the Sharpless asymmetric dihydroxylation has never been employed as the sole source of chirality for this purpose.

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7

Morikawa, Kouhei, and K. Barry Sharpless. "Double diastereoselection in asymmetric dihydroxylation." Tetrahedron Letters 34, no. 35 (August 1993): 5575–78. http://dx.doi.org/10.1016/s0040-4039(00)73885-8.

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8

Feng, Zhi-Xiang, and Wei-Shan Zhou. "Asymmetric dihydroxylation of heteroaromatic acrylates." Tetrahedron Letters 44, no. 3 (January 2003): 493–95. http://dx.doi.org/10.1016/s0040-4039(02)02605-9.

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9

STINSON, STEPHEN. "Asymmetric Dihydroxylation Of Olefins Achieved." Chemical & Engineering News 66, no. 12 (March 21, 1988): 19–20. http://dx.doi.org/10.1021/cen-v066n012.p019.

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10

Fleming, Steven A., Renmao Liu, and J. Ty Redd. "Asymmetric dihydroxylation of disubstituted allenes." Tetrahedron Letters 46, no. 47 (November 2005): 8095–98. http://dx.doi.org/10.1016/j.tetlet.2005.09.138.

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11

JOHNSON, R. A., and K. B. SHARPLESS. "ChemInform Abstract: Catalytic Asymmetric Dihydroxylation." ChemInform 25, no. 17 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199417299.

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12

KOLB, C. H., M. S. VANNIEUWENHZE, and K. B. SHARPLESS. "ChemInform Abstract: Catalytic Asymmetric Dihydroxylation." ChemInform 26, no. 9 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199509300.

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13

Becker, Heinrich, Marcos A. Soler, and K. Barry Sharpless. "Selective asymmetric dihydroxylation of polyenes." Tetrahedron 51, no. 5 (January 1995): 1345–76. http://dx.doi.org/10.1016/0040-4020(94)01021-q.

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14

Caddick, Stephen, Sakthitharan Shanmugathasan, Denis Brasseur, and Vern M. Delisser. "Asymmetric dihydroxylation of homoallylic enynols." Tetrahedron Letters 38, no. 32 (August 1997): 5735–36. http://dx.doi.org/10.1016/s0040-4039(97)01259-8.

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15

Dethe, Dattatraya H., and Vijay Kumar B. "Concise asymmetric total synthesis of bruceolline J." Organic Chemistry Frontiers 2, no. 5 (2015): 548–51. http://dx.doi.org/10.1039/c5qo00030k.

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16

Cernerud, Magnus, JoséAntonio Reina, Jörgen Tegenfeldt, and Christina Moberg. "Chiral polymers via asymmetric epoxidation and asymmetric dihydroxylation." Tetrahedron: Asymmetry 7, no. 10 (October 1996): 2863–70. http://dx.doi.org/10.1016/0957-4166(96)00377-1.

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17

Lindsay, Karl B., and Stephen G. Pyne. "Asymmetric Synthesis of ( - )-Swainsonine." Australian Journal of Chemistry 57, no. 7 (2004): 669. http://dx.doi.org/10.1071/ch04009.

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This paper describes a new synthesis of (–)-swainsonine via the ring-closing metathesis reaction of a substituted 3-allyl-4-vinyloxazolindin-2-one and subsequent diastereoselective syn-dihydroxylation of the resulting pyrrolo- [1,2-c]oxazol-3-one.

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18

Hikaambo, Christabel Nang’andu, Hanzooma Hatwiko, Derick Munkombwe, Aubrey Chichonyi Kalungia, Chiluba Mwila, Steward Mudenda, Ronald Kampamba Mutati, Martin Kampamba, and Hee Doo Kim. "Synthesis of enantiomerically pure (d) – doxylamine using a novel chiral auxiliary." International Journal of Biological and Chemical Sciences 15, no. 5 (January 24, 2022): 2161–70. http://dx.doi.org/10.4314/ijbcs.v15i5.35.

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It is known that the main mode of synthesis of doxylamine is a racemic mixture. However, the active enantiomers of the compound show superior activity to that of the racemate, thus the need to synthesize doxylamine as an enantiopure compound. This study aimed to synthesise an enantiopure (d)-doxylamine and it was achieved through the use of optically active diols synthesised from a novel chiral auxiliary. While most available methods employ Sharpless asymmetric dihydroxylation, this study reports a method that achieves superior enantiomeric excess with consequent better yields of 67% of end products not easily accessible by use of Sharpless Asymmetric Dihydroxylation.

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19

Wang, Zhi-Min, Xiu-Lian Zhang, and K. Barry Sharpless. "Asymmetric dihydroxylation of aryl allyl ethers." Tetrahedron Letters 34, no. 14 (April 1993): 2267–70. http://dx.doi.org/10.1016/s0040-4039(00)77590-3.

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20

Jacobsen, Eric N., Istvan Marko, William S. Mungall, Georg Schroeder, and K. Barry Sharpless. "Asymmetric dihydroxylation via ligand-accelerated catalysis." Journal of the American Chemical Society 110, no. 6 (March 1988): 1968–70. http://dx.doi.org/10.1021/ja00214a053.

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21

Morikawa, Kouhei, Jeonghan Park, Pher G. Andersson, Tomiki Hashiyama, and K. Barry Sharpless. "Catalytic asymmetric dihydroxylation of tetrasubstituted olefins." Journal of the American Chemical Society 115, no. 18 (September 1993): 8463–64. http://dx.doi.org/10.1021/ja00071a072.

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22

Xu, Daqiang, Gerard A. Crispino, and K. Barry Sharpless. "Selective asymmetric dihydroxylation (AD) of dienes." Journal of the American Chemical Society 114, no. 19 (September 1992): 7570–71. http://dx.doi.org/10.1021/ja00045a043.

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23

Show, Krishanu, Puspesh K. Upadhyay, and Pradeep Kumar. "An asymmetric dihydroxylation route to (−)-bulgecinine." Tetrahedron: Asymmetry 22, no. 11 (June 2011): 1234–38. http://dx.doi.org/10.1016/j.tetasy.2011.06.018.

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24

Soderquist, John A., Anil M. Rane, and Carlos J. López. "Asymmetric dihydroxylation of vinyl and allylsilanes." Tetrahedron Letters 34, no. 12 (March 1993): 1893–96. http://dx.doi.org/10.1016/s0040-4039(00)91956-7.

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25

Wang, Zhi-Min, and K. Barry Sharpless. "Asymmetric dihydroxylation of tertiary allylic alcohols." Tetrahedron Letters 34, no. 51 (December 1993): 8225–28. http://dx.doi.org/10.1016/s0040-4039(00)61396-5.

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26

Bolm, Carsten, and Arne Gerlach. "Asymmetric dihydroxylation with silica-anchored alkaloids." Chemical Communications, no. 24 (1997): 2353–54. http://dx.doi.org/10.1039/a706605h.

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27

Nelson, Adam, and Stuart Warren. "Asymmetric dihydroxylation of allylic phosphine oxides." Journal of the Chemical Society, Perkin Transactions 1, no. 17 (1997): 2645–58. http://dx.doi.org/10.1039/a700374i.

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28

Bhunnoo, Riaz A., Yulai Hu, Dramane I. Lainé, and Richard C. D. Brown. "An Asymmetric Phase-Transfer Dihydroxylation Reaction." Angewandte Chemie International Edition 41, no. 18 (September 16, 2002): 3479–80. http://dx.doi.org/10.1002/1521-3773(20020916)41:18<3479::aid-anie3479>3.0.co;2-o.

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29

Maier, Martin E., and Sebastian Reuter. "Double Asymmetric Dihydroxylation of 1,5-Hexadiene." Liebigs Annalen 1997, no. 10 (October 1997): 2043–46. http://dx.doi.org/10.1002/jlac.199719971006.

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30

JEONG, K. S., P. SJOE, and K. B. SHARPLESS. "ChemInform Abstract: Asymmetric Dihydroxylation of Enynes." ChemInform 23, no. 52 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199252107.

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31

Sayyed, Iliyas A., Vinay V. Thakur, Milind D. Nikalje, Gajanan K. Dewkar, S. P. Kotkar, and A. Sudalai. "Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation." Tetrahedron 61, no. 11 (March 2005): 2831–38. http://dx.doi.org/10.1016/j.tet.2005.01.074.

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32

Zhou, Gang, Xiaolei Gao, Zhe Zhang, and Yulin Li. "A Synthesis of the C-11 Epimer of the Sesquiterpenoid 5-epi-kudtriol." Journal of Chemical Research 2000, no. 4 (April 2000): 174–75. http://dx.doi.org/10.3184/030823400103166841.

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33

Lu, Kui, Ming Li, Yuna Huang, Yuanyuan Sun, Zhi Gong, Qijun Wei, Xia Zhao, Yongmin Zhang, and Peng Yu. "Total synthesis of wikstrol A and wikstrol B." Organic & Biomolecular Chemistry 17, no. 35 (2019): 8206–13. http://dx.doi.org/10.1039/c9ob01219b.

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34

Kauloorkar, Shruti Vandana, Vishwajeet Jha, Ganesh Jogdand, and Pradeep Kumar. "A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (−)-lentiginosine, (−)-epi-lentiginosine and (−)-dihydroxypyrrolizidine." Org. Biomol. Chem. 12, no. 25 (2014): 4454–60. http://dx.doi.org/10.1039/c4ob00461b.

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The total synthesis of (−)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.

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35

Bassindale, Alan R., Peter G. Taylor, and Youli Xu. "Asymmetric dihydroxylation of vinyl- and allyl-silanes." Journal of the Chemical Society, Perkin Transactions 1, no. 8 (1994): 1061. http://dx.doi.org/10.1039/p19940001061.

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36

Belley, Michel L., Bryan Hill, Hugh Mitenko, John Scheigetz, and Robert Zamboni. "Asymmetric Dihydroxylation of Dienes: Synthesis of Tetrols." Synlett 1996, no. 01 (January 1996): 92–94. http://dx.doi.org/10.1055/s-1996-5323.

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37

Brimble, Margaret A., Daryl D. Rowan, and Julie A. Spicer. "Asymmetric dihydroxylation of α- and β-farnesene." Tetrahedron Letters 35, no. 50 (December 1994): 9445–46. http://dx.doi.org/10.1016/s0040-4039(00)78566-2.

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38

Bonini, Carlo, Maurizio D'Auria, and Pietro Fedeli. "First controlled asymmetric dihydroxylation of thiophene acrylates." Tetrahedron Letters 43, no. 21 (May 2002): 3813–15. http://dx.doi.org/10.1016/s0040-4039(02)00688-3.

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39

Gupta, Priti, Rodney A. Fernandes, and Pradeep Kumar. "An asymmetric dihydroxylation route to (S)-oxybutynin." Tetrahedron Letters 44, no. 22 (May 2003): 4231–32. http://dx.doi.org/10.1016/s0040-4039(03)00886-4.

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40

Wang, Zhi-Min, and K. Barry Sharpless. "Asymmetric Dihydroxylation of α-Substituted Styrene Derivatives." Synlett 1993, no. 08 (1993): 603–4. http://dx.doi.org/10.1055/s-1993-22547.

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41

Wang, Lisa, and K. Barry Sharpless. "Catalytic asymmetric dihydroxylation of cis-disubstituted olefins." Journal of the American Chemical Society 114, no. 19 (September 1992): 7568–70. http://dx.doi.org/10.1021/ja00045a042.

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42

Iwashima, Makoto, Takeshi Kinsho, and Amos B. Smith. "A caveat on the Sharpless asymmetric dihydroxylation." Tetrahedron Letters 36, no. 13 (March 1995): 2199–202. http://dx.doi.org/10.1016/0040-4039(95)00274-g.

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43

Ahrgren, Leif, and Lori Sutin. "Sharpless Asymmetric Dihydroxylation on an Industrial Scale." Organic Process Research & Development 1, no. 6 (November 1997): 425–27. http://dx.doi.org/10.1021/op970030v.

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44

Jefford, Charles W., and Géza Timári. "Amplified asymmetric dihydroxylation of a racemic cyclopentene." J. Chem. Soc., Chem. Commun., no. 15 (1995): 1501–2. http://dx.doi.org/10.1039/c39950001501.

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45

de Boer, Johannes W., Wesley R. Browne, Syuzanna R. Harutyunyan, Laura Bini, Theodora D. Tiemersma-Wegman, Paul L. Alsters, Ronald Hage, and Ben L. Feringa. "Manganese catalysed asymmetric cis-dihydroxylation with H2O2." Chemical Communications, no. 32 (2008): 3747. http://dx.doi.org/10.1039/b808355j.

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46

MORIKAWA, K., and K. B. SHARPLESS. "ChemInform Abstract: Double Diastereoselection in Asymmetric Dihydroxylation." ChemInform 24, no. 52 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199352071.

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47

Bonini, Carlo, Maurizio D'Auria, and Pietro Fedeli. "First Controlled Asymmetric Dihydroxylation of Thiophene Acrylates." ChemInform 33, no. 35 (May 20, 2010): 115. http://dx.doi.org/10.1002/chin.200235115.

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48

Bolm, Carsten, and Arne Gerlach. "Asymmetric Dihydroxylation with MeO-Polyethyleneglycol-Bound Ligands." Angewandte Chemie International Edition in English 36, no. 7 (April 18, 1997): 741–43. http://dx.doi.org/10.1002/anie.199707411.

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49

XU, D., G. A. CRISPINO, and K. B. SHARPLESS. "ChemInform Abstract: Selective Asymmetric Dihydroxylation of Dienes." ChemInform 24, no. 1 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199301132.

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50

CADDICK, S., S. SHANMUGATHASAN, D. BRASSEUR, and V. M. DELISSER. "ChemInform Abstract: Asymmetric Dihydroxylation of Homoallylic Enynols." ChemInform 28, no. 46 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199746043.

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