Asymmetric reduction of carbonyl compounds by yeast. IV. Preparation of optically active β-hydroxy sulfides, sulfoxides and sulfones

1978 ◽  
Vol 31 (9) ◽  
pp. 1965 ◽  
Author(s):  
RL Crumbie ◽  
BS Deol ◽  
JE Nemorin ◽  
DD Ridley
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Optically Active ◽  
Secondary Alcohols ◽  
Optically Pure

Reduction of simple β-keto sulfides, β-keto sulfoxides and P-keto sulfones by an actively fermenting mutant of Saccharomyces cerevisiae proceeds readily and affords good yields of the corresponding optically active secondary alcohols. For example, 1-(benzylthio)propan-2-one gave optically pure (S)-(+)-1-(benzylthio)propan-2-ol and 1- (phenylsulfonyl)propan-2-one gave optically pure (S)-(+)-1- (phenylsulfonyl)propan-2-ol. In the reductions of racemic β-keto sulfoxides the enantiomers were reduced at sufficiently different rates to enable isolation of an optically active ketone and of an optically active β-hydroxy sulfoxide. Hence, 1-(phenylsulfinyl)propan-2-one gave (S)-(-)-1-(phenyl-sulfinyl)propan-2-one and (RS,SC)-(+)-1- (phenylsulfinyl)propan-2-ol.

Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivatives

1976 ◽  
Vol 29 (11) ◽  
pp. 2459 ◽  
Author(s):  
BS Deol ◽  
DD Ridley ◽  
GW Simpson
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Ethyl Pyruvate ◽  
Optically Active ◽  
Phenyl Acetate ◽  
Keto Esters ◽  
Hydroxy Carboxylic Acid ◽  
Hydroxy Esters ◽  
Optically Pure

α- and β-Keto esters and amides are readily reduced by an actively fermenting mutant of Saccharomyces cerevisiae and produce optically active α- and β-hydroxy esters and amides in moderate yields. Typically, methyl 2-oxo-2-phenylacetate gave methyl (R)-(-)-2-hydroxy- 2-phenyl- acetate; 2-oxo-2-phenylacetamide gave (R)-(-)-2-hydroxy-2- phenylacetamide; ethyl benzoylacetate gave ethyl (S)-(-)-3-hydroxy-3- phenylpropionate, and ethyl 2-oxocyclohexanecarboxylate gave ethyl (1R,2S)-(+)-2-hydroxycyclohexanecarboxylate. In each case, the product obtained was optically pure. However, the reduction of ethyl pyruvate to ethyl lactate produced partially racemized products.

Preparation of secondary alcohols of high optical purity

1986 ◽  
Vol 51 (2) ◽  
pp. 401-403 ◽  
Author(s):  
Otakar Červinka ◽  
Anna Fábryová ◽  
Irina Sablukova
Keyword(s):  
Nmr Spectroscopy ◽  
Optical Purity ◽  
Optically Active ◽  
Secondary Alcohols ◽  
Lithium Aluminium Hydride ◽  
Enantioselective Reduction ◽  
H Nmr ◽  
Lithium Aluminium ◽  
High Optical Purity ◽  
Optically Pure

Partially resolved enantiomers of optically active alcohols I-V, obtained by enantioselective reduction of the corresponding ketones with lithium aluminium hydride in the presence of (-)-quinine, were converted into crystalline 3,5-dinitrobenzoates or phenylcarbamates. The esters of the nearly optically pure enantiomers were separated by crystallization from the generally more soluble esters of the racemates. Optical purity of the hydrolytically liberated alcohols was determined by 1H NMR spectroscopy in the presence of chiral shifting agents.

scholarly journals Synthesis of 2-Amino-apopinan-3-ol and Applications of Its Derivatives in Asymmetric Reduction of Ketones

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 63
Author(s):  
Anna Kmieciak ◽  
Marek P. Krzemiński
Keyword(s):  
Amino Alcohol ◽  
Asymmetric Reduction ◽  
Optically Active ◽  
Asymmetric Reactions ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Active Compounds ◽  
Reduction Methods ◽  
Optically Pure ◽  
Reduction Of Ketones

Monoterpenes are optically active compounds which occur in nature. This fact makes them interesting precursors for the synthesis of optically active ligands, which can be applied in various asymmetric reactions. In this work, we present the synthesis of optically pure 2-amino-apopinan-3-ol from (−)-α-pinene. The obtained amino alcohol was used as a precursor of oxazaborolidine, which was used as catalyst in the asymmetric reduction of aryl-alkyl ketones with borane. In the second part, we transformed 2-amino-apopinan-3-ol into PHOX ligand in a three-step reaction. The complex of ruthenium precursor with PHOX ligand was used as a catalyst in the asymmetric transfer hydrogenation of aryl-alkyl ketones. Alcohols with enantiomeric excesses of up to 97% were isolated using both reduction methods.

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

Practical Synthesis of Optically Pure Methyl (2R,3S)-2,3-Epoxybutanoate via Microbial Asymmetric Reduction of α-Chloroacetoacetate

Synthesis ◽  
1993 ◽  
Vol 1993 (05) ◽  
pp. 513-516 ◽  
Author(s):  
Hiroyuki Akita ◽  
Reiko Todoroki ◽  
Hiroshi Endo ◽  
Yoshinobu Ikari ◽  
Takeshi Oishi
Keyword(s):  
Asymmetric Reduction ◽  
Practical Synthesis ◽  
Optically Pure

Green asymmetric reduction of acetophenone derivatives: Saccharomyces cerevisiae and aqueous natural deep eutectic solvent

2018 ◽  
Vol 41 (2) ◽  
pp. 253-262 ◽  
Author(s):  
Manuela Panić ◽  
Doris Delač ◽  
Marin Roje ◽  
Ivana Radojčić Redovniković ◽  
Marina Cvjetko Bubalo
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Asymmetric Reduction ◽  
Deep Eutectic Solvent ◽  
Acetophenone Derivatives ◽  
Natural Deep Eutectic Solvent
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