THE PRODUCT OF BAKERS-YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL

被引：13

作者：

HAMDANI, M ^{[1
]}

DEJESO, B ^{[1
]}

DELEUZE, H ^{[1
]}

SAUX, A ^{[1
]}

MAILLARD, B ^{[1
]}

机构：

[1] UNIV BORDEAUX 1,CHIM ORGAN LAB,CNRS,URA 35,351 COURS LIBERAT,F-33405 TALENCE,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(00)80233-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2-acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in order to obtain enantiomerically enriched compounds. In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reduction of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate. This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radical and the diastereoselectivity of the addition of this intermediate to alkenes was studied.

引用

页码：1233 / 1236

页数：4

共 50 条

[21] ENANTIOSPECIFIC SYNTHESIS OF OPTICALLY PURE (S)-(+)-3-HYDROXY-1-PHENYL-1-BUTANONE BY BAKERS-YEAST REDUCTION
CHENEVERT, R
THIBOUTOT, S
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (08): : 1599 - 1601
[22] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .7. ENANTIOSELECTIVE REDUCTION OF 2-METHYL-3-OXOPROPIONATE BY BAKERS-YEAST
NAKAMURA, K
MIYAI, T
USHIO, K
OKA, S
OHNO, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (06) : 2089 - 2093
[23] ENANTIOSELECTIVE SYNTHESIS OF (S)-2-METHYL-1-ALKANOLS VIA BAKERS-YEAST MEDIATED REDUCTION OF ALPHA-METHYL-2-THIOPHENEPROPENALS
HOGBERG, HE
HEDENSTROM, E
FAGERHAG, J
SERVI, S
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07): : 2052 - 2059
[24] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF 2-METHYL-3-OXOALKANOIC ACIDS BY USE OF FERMENTING BAKERS-YEAST
WATABU, H
OHKUBO, M
MATSUBARA, H
SAKAI, T
TSUBOI, S
UTAKA, M
CHEMISTRY LETTERS, 1989, (12) : 2183 - 2184
[25] ENZYMES PRODUCING 2 CHIRAL CENTERS .1. PURIFICATION AND PROPERTIES OF AN ASYMMETRIC REDUCTION ENZYME OF 2-METHYL-3-OXOBUTYRATE IN BAKERS-YEAST
FURUICHI, A
AKITA, H
MATSUKURA, H
OISHI, T
HORIKOSHI, K
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (09): : 2563 - 2570
[26] ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-5,5,5-TRIFLUORO-4-HYDROXY-2-PENTANONE BY BAKERS-YEAST REDUCTION
BUCCIARELLI, M
FORNI, A
MORETTI, I
PRATI, F
TORRE, G
GAZZETTA CHIMICA ITALIANA, 1990, 120 (02): : 99 - 100
[27] BAKERS-YEAST REDUCTION OF ALPHA-(ACYLAMINO)ACETOPHENONES AND LIPASE-CATALYZED RESOLUTION OF 2-ACYLAMINO-1-ARYLETHANOLS
IZUMI, T
FUKAYA, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (04) : 1216 - 1221
[28] ASYMMETRIC REDUCTION OF 1-ACETOXY-2-ALKANONES WITH BAKERS-YEAST - PURIFICATION AND CHARACTERIZATION OF ALPHA-ACETOXY KETONE REDUCTASE
ISHIHARA, K
NAKAJIMA, N
TSUBOI, S
UTAKA, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (12) : 3314 - 3319
[29] REGIOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (S)-1-ACETOXY-2-HYDROXY-4-ALKANONES BY USE OF BAKERS-YEAST REDUCTION OF 1-ACETOXY-2,4-ALKANEDIONES
UTAKA, M
ITO, H
MIZUMOTO, T
TSUBOI, S
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) : 685 - 686
[30] Diastereoselectivity in the bakers yeast reduction of [1-H-2](sorboaldehyde)Fe(CO)(3)
Howell, JAS
OLeary, PJ
Palin, MG
Jaouen, G
Top, S
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 307 - 315

← 1 2 3 4 5 →