ENZYME-CATALYZED SYNTHESIS OF (R)-KETONE-CYANOHYDRINS AND THEIR HYDROLYSIS TO (R)-ALPHA-HYDROXY-ALPHA-METHYL-CARBOXYLIC ACIDS

被引：67

作者：

EFFENBERGER, F

HORSCH, B

WEINGART, F

ZIEGLER, T

KUHNER, S

机构：

[1] Institut für Organische Chemie, Universität Stuttgart Pfaffenwaldring 55

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)78796-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(R)-Ketone-cyanohydrins (R)-2 are obtained with high enantioselectivity from aliphatic ketones 1 and HCN in organic solvents using (R)-oxynitrilase (EC 4.1.2.10) as catalyst. Acid catalyzed hydrolysis of the cyanohydrins (R)-2 affords the corresponding (R)-alpha-hydroxy-alpha-methyl-carboxylic acids (R)-3 without measurable racemization.

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页码：2605 / 2608

页数：4

相关论文

共 26 条

[1]

Bindra J. S., 1981, TOTAL SYNTHESIS NATU, V4, P353

[2] SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HYDROXY ACIDS BY ADDITION OF ORGANOZINE COMPOUNDS TO (-)MENTHYL PHENYLGLYOXALATE [J].

BOIREAU, G ;

DEBERLY, A ;

ABENHAIM, D .

TETRAHEDRON, 1989, 45 (18) :5837-5844

[3] ABSOLUTE CONFIGURATION OF 2-HYDROXY-2-METHYLBUTYRIC ACID [J].

CHRISTENSEN, BW ;

KJAER, A .

ACTA CHEMICA SCANDINAVICA, 1962, 16 (10) :2466-&

[4]

DALE JA, 1969, J ORG CHEM, V34, P2534

[5]

EFENBERGER F, 1991, LIEBIGS ANN CHEM

[6] ENZYME-CATALYZED CYANOHYDRIN SYNTHESIS IN ORGANIC-SOLVENTS [J].

EFFENBERGER, F ;

ZIEGLER, T ;

FORSTER, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (05) :458-460

[7] ENZYME-CATALYZED REACTIONS .5. ENZYME-CATALYZED SYNTHESIS OF (S)-CYANOHYDRINS AND SUBSEQUENT HYDROLYSIS TO (S)-ALPHA-HYDROXY-CARBOXYLIC ACIDS [J].

EFFENBERGER, F ;

HORSCH, B ;

FORSTER, S ;

ZIEGLER, T .

TETRAHEDRON LETTERS, 1990, 31 (09) :1249-1252

[8] AN IMPROVED METHOD OF PREPARING TESTOSTERONE, DIHYDROTESTOSTERONE AND SOME OF THEIR ESTERS [J].

ERCOLI, A ;

DERUGGIERI, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (03) :650-653

[9] PERMETHYL-BETA-CYCLODEXTRIN, CHEMICALLY BONDED TO POLYSILOXANE - A CHIRAL STATIONARY PHASE WITH WIDER APPLICATION RANGE FOR ENANTIOMER SEPARATION BY CAPILLARY GAS-CHROMATOGRAPHY [J].

FISCHER, P ;

AICHHOLZ, R ;

BOLZ, U ;

JUZA, M ;

KRIMMER, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (04) :427-429

[10] ENANTIOSELECTIVE FUNCTIONALIZATION OF PROCHIRAL DIOLS VIA CHIRAL SPIROKETALS - PREPARATION OF OPTICALLY PURE 2-SUBSTITUTED 1,3-PROPANEDIOL DERIVATIVES AND ASYMMETRIC-SYNTHESIS OF CHROMAN RING AND SIDE-CHAIN OF ALPHA-TOCOPHEROL [J].

HARADA, T ;

HAYASHIYA, T ;

WADA, I ;

IWAAKE, N ;

OKU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :527-532