REGIOSELECTIVE AND ENANTIOSELECTIVE BIOREDUCTION OF ETHYL 2,4-DIOXOALKANOATES AND GAMMA-KETO-ALPHA-ENAMINO ESTERS WITH FERMENTING BAKERS-YEAST

被引：13

作者：

BARALDI, PG ^{[1
]}

MANFREDINI, S ^{[1
]}

POLLINI, GP ^{[1
]}

ROMAGNOLI, R ^{[1
]}

SIMONI, D ^{[1
]}

ZANIRATO, V ^{[1
]}

机构：

[1] UNIV FERRARA,DIPARTIMENTO SCI FARMACEUT,VIA FOSSATO MORTARA 17-19,I-44100 FERRARA,ITALY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 20期

关键词：

2,4-DIOXOALKANOATES, GAMMA-KETO-ALPHA-ENAMINO ESTERS, BAKERS YEAST, ALPHA-HYDROXY-GAMMA-KETOESTERS, PIG LIVER ESTERASE;

D O I：

10.1016/S0040-4039(00)78883-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,4-Dioxoalkanoates 1a-d and the parent compounds gamma-keto-alpha-enamino esters 2a-d are regioselectively reduced by baker's yeast to (R)-alpha-hydroxy-gamma-ketoesters 4a-d in moderate to good chemical yield and appreciable enantioselectivity. Pig liver esterase enantioselective hydrolysis of the acetyl derivatives 3a-d, easily obtained by treatment of racemic alpha-hydroxy-gamma-keto esters 4a-d, produced the optically active (S) 4a-d in good chemical (60-92%) and optical (53-92%) yield.

引用

页码：2871 / 2874

页数：4

共 10 条

[1] AKITA H, 1983, CHEM PHARM BULL, V31, P4384
[2] ETHYL 5-SUBSTITUTED-3-ISOXAZOLECARBOXYLATES AS STARTING MATERIALS FOR A CONVENIENT ROUTE TO 3(2H)FURANONES AND 3(2H)IMINOFURANES
BARALDI, PG
BARCO, A
BENETTI, S
MANFREDINI, S
POLLINI, GP
SIMONI, D
[J]. TETRAHEDRON LETTERS, 1984, 25 (38) : 4313 - 4316
[3] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[4] DOEL BS, 1976, AUST J CHEM, V29, P2459
[5] HOUSE HO, 1972, MODERN SYNTHETIC REA, P492
[6] A CONVENIENT SYNTHESIS OF GAMMA-OXO-ACRYLATES
MANFREDINI, S
SIMONI, D
ZANIRATO, V
CASOLARI, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (32) : 3997 - 4000
[7] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .5. EFFECT OF ALLYL ALCOHOL ON REDUCTION OF BETA-KETO-ESTERS BY BAKERS-YEAST
NAKAMURA, K
INOUE, K
USHIO, K
OKA, S
OHNO, A
[J]. CHEMISTRY LETTERS, 1987, (04) : 679 - 682
[8] SERVI S, 1990, SYNTHESIS-STUTTGART, P1
[9] SUEMUNE H, 1987, CHEM PHARM BULL, V35, P3112
[10] REGIOSELECTIVE AND ENANTIOSELECTIVE REDUCTION OF ALPHA,2-DIOXOCYCLOALKANEACETATES WITH FERMENTING BAKERS-YEAST - A NEW SYNTHESIS OF (R)-(-)-HEXAHYDROMANDELIC ACID
TSUBOI, S
NISHIYAMA, E
FURUTANI, H
UTAKA, M
TAKEDA, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) : 1359 - 1362

← 1 →