Synthetic approach to optically pure trifluoromethylated compounds

Kitazume, Tomoya; Lin, J. T.

doi:10.1016/s0022-1139(00)85187-8

Cited by 16 publications

(3 citation statements)

References 19 publications

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“…[15][16][17][18][19][20][21][22][23][24][25][26] Recently, Smallridge et al, 56 North, 57 and Rotthaus et al 58 have shown that similar reductions are possible using non-fermenting yeast in an organic solvent. Finally, we would like to report our results concerning the reduction of six ketones 1a-3a and 1b-3b utilizing Baker's yeast/water or Baker's yeast/organic solvent reaction system (Scheme 6).…”

Section: Baker's Yeast Mediated Reduction Of Ketones 1a-3a and 1b-3b mentioning

confidence: 99%

“…In recent years Baker's yeast (Saccharomyces cerevisiae) has gained increasing importance in view of applications in asymmetric synthesis. 15, 16 Among the numerous enzymes in Baker's yeast, oxidoreductases play an important role for reductions of ketones with chloro-, 17 bromo-, 18 perfluoroalkyl-, 19 nitro-, 20,21 hydroxyl-, 22,23 dithianyl-, 24 and even silyl- 25 and germyl- 26 moieties. Thus, we also report our results on the Baker's yeast mediated stereoselective reduction of the ketones 1a-3a and 1b-3b (Scheme 1) as another possible route to optically active alcohols 7a-9a and 7b-9b (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

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Preparation of various enantiomerically pure (benzotriazol-1-yl)- and (benzotriazol-2-yl)-alkan-2-ols

Pchelka

Loupy

Petit

2006

Tetrahedron: Asymmetry

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Section: Baker's Yeast Mediated Reduction Of Ketones 1a-3a and 1b-3b mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of various enantiomerically pure (benzotriazol-1-yl)- and (benzotriazol-2-yl)-alkan-2-ols

Pchelka

Loupy

Petit

2006

Tetrahedron: Asymmetry

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“…If one of the moieties on the ketone is a long chain, the other has to be methyl for the yeast to accept it [247][248]. Molecules containing functional groups adjacent to the ketone were successfully reduced as well: halogens [249][250], hydroxyl [251], perfluoroalkyl [252], silyl [253], and germyl [254].…”

Section: Whole Cells and Redox Reactionsmentioning

confidence: 99%

Redox Enzymes Used in Chiral Syntheses Coupled to Coenzyme Regeneration

Leonida¹

2001

CMC

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Due to their ability to perform reactions in a stereo- and regiospecific manner, while functioning under mild conditions of temperature and pH, enzymes are increasingly used for chiral synthesis in the pharmaceutical industry, in medicinal chemistry, agriculture, cosmetic and food industry. The oxidoreductases as catalysts require a coenzyme (cofactor) which functions as an electron carrier. If used in stoichiometric amounts the cost of coenzymes makes synthetic applications of redox enzymes prohibitively expensive for industrial applications. The present review updates previous discussions about the objectives of cofactor regeneration as a requirement for the applicability of enzymatic redox reactions, and about the strategies customarily used to this end. Different types of chiral syntheses coupled successfully to coenzyme regeneration (amino acid synthesis, lactone synthesis, synthetic reactions involving alcohols, hydroxy acid and steroid synthesis, deracemization) are then discussed. New catalysts, cross-linked enzyme crystals, prepared from redox enzyme are presented in a small paragraph together with some of their applications. Special attention is given to whole cells used in this type of synthesis and their advantages and disadvantages are presented in one paragraph. Finally, different reactors, within which were conducted chiral syntheses catalyzed by oxireductases and coupled to cofactor regeneration, are briefly discussed.

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