Reduction of alkyl (2-oxocyclohexyl)acetates by baker's yeast

被引：10

作者：

Ganaha, M ^{[1
]}

Funabiki, Y ^{[1
]}

Motoki, M ^{[1
]}

Yamauchi, S ^{[1
]}

Kinoshita, Y ^{[1
]}

机构：

[1] Ehime Univ, Fac Agr, Dept Agr Chem, Matsuyama, Ehime 790, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 1998年 / 62卷 / 01期

关键词：

yeast-reduction; gamma-ketoester; kinetic resolution; asymmetric reduction;

D O I：

10.1271/bbb.62.181

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Baker's yeast reduction of methyl and ethyl (2-oxocyclohexyl)acetates proceeded with enantio-and diastereo-selectivity, affording the corresponding (2S)-trans-alcohols (major), (2S)-cis-alcohols (minor), and the unaltered (1S)-ketones with high optical purity.

引用

页码：181 / 184

页数：4

共 22 条

[1] REARRANGEMENT OF DICHLOROCYCLOPROPANE IN PRESENCE OF INTERNAL NUCLEOPHILE - ABSENCE OF INTRAMOLECULAR PARTICIPATION - CONCERTED REARRANGEMENT IN ALLYLIC CHLORIDE [J].

CHICHE, L ;

CHRISTOL, H ;

COSTE, J ;

PIETRASANTA, F ;

PLENAT, F .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (01) :164-174

[2] PREPARATION OF AN OPTICALLY-ACTIVE INTERMEDIATE FOR SYNTHESIS OF PROSTAGLANDINS [J].

COREY, EJ ;

SNIDER, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :256-258

[3] GAMMA-KETO-GAMMA-PHENYLBUTYRAMIDES AND GAMMA-HYDROXY-GAMMA-PHENYLBUTYRAMIDES - SYNTHESIS, ABSORPTION SPECTRA AND STRUCTURE STUDIES [J].

CROMWELL, NH ;

COOK, KE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4573-4577

[4]

Fr?ter G., 1980, HELV CHIM ACTA, V63, P1383

[5] ASYMMETRIC REDUCTION WITH BAKER YEAST [J].

FUJISAWA, T ;

SATO, T ;

ITOH, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1986, 44 (06) :519-531

[6] ENANTIOSELECTIVE REDUCTION OF 4-OXO-3-TETRAHYDROTHIOPYRANYL-ACETATES WITH BAKERS-YEAST AND APPLICATION TO THE SYNTHESIS OF A PROSTAGLANDIN INTERMEDIATE IN OPTICALLY PURE FORM [J].

FUJISAWA, T ;

MOBELE, BI ;

SHIMIZU, M .

TETRAHEDRON LETTERS, 1991, 32 (48) :7055-7058

[7] A CHEMOENZYMATIC SYNTHESIS OF LEUKOTRIENE-B4 [J].

HAN, CQ ;

DITULLIO, D ;

WANG, YF ;

SIH, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) :1253-1258

[8]

HIROI K, 1972, CHEM PHARM BULL, V20, P246

[9] FLUORIDE-MEDIATED REACTIONS OF ENOL SILYL ETHERS - REGIOSPECIFIC MONOALKYLATION OF KETONES [J].

KUWAJIMA, I ;

NAKAMURA, E ;

SHIMIZU, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :1025-1030

[10] ELECTROREDUCTIVE CYCLIZATION - KETONES AND ALDEHYDES TETHERED TO ALPHA,BETA-UNSATURATED ESTERS (NITRILES) - FUNDAMENTAL INVESTIGATIONS [J].

LITTLE, RD ;

FOX, DP ;

VANHIJFTE, L ;

DANNECKER, R ;

SOWELL, G ;

WOLIN, RL ;

MOENS, L ;

BAIZER, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2287-2294

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