Stereoselective chemoenzymatic synthesis of both enantiomers of protected 4-amino-2-pentanone

被引：20

作者：

Besse, P ^{[1
]}

Ciblat, S

Canet, JL

Troin, Y

Veschambre, H

机构：

[1] Univ Blaise Pascal, Lab Synth Electrosynth & Etud Syst Interet Biol, CNRS, UMR 6504, F-63177 Aubiere, France

[2] Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, EA 987, F-63174 Aubiere, France

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(99)00234-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An acetal protected 4-amino-2-pentanone was synthesised by two different routes in 10 and seven steps, respectively, the key step being a microbiological reduction. Both enantiomers of the amine were obtained enantiomerically pure. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2213 / 2224

页数：12

相关论文

共 50 条

[1]

BARBOT F, 1983, SYNTHESIS-STUTTGART, P651

[2]

BARDOT V, 1996, THESISU B PASCAL CLE

[3] Nucleophilic substitution of (alkoxymethylene)dimethylammonium chloride with potassium phthalimide; A convenient procedure for the synthesis of imides with inversion of configuration [J].

Barrett, AGM ;

Braddock, DC ;

James, RA ;

Procopiou, PA .

CHEMICAL COMMUNICATIONS, 1997, (05) :433-434

[4] USE OF BIOLOGICAL-SYSTEMS FOR THE PREPARATION OF CHIRAL MOLECULES .3. AN APPLICATION IN PHEROMONE SYNTHESIS - PREPARATION OF SULCATOL ENANTIOMERS [J].

BELAN, A ;

BOLTE, J ;

FAUVE, A ;

GOURCY, JG ;

VESCHAMBRE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :256-260

[5] CHEMOENZYMATIC SYNTHESIS OF ALPHA-BICHIRAL SYNTHONS - APPLICATION TO THE PREPARATION OF CHIRAL EPOXIDES [J].

BESSE, P ;

VESCHAMBRE, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1271-1285

[6] CHEMOENZYMATIC SYNTHESIS OF CHIRAL EPOXIDES - PREPARATION OF 4-PHENYL-2,3-EPOXYBUTANE AND 1-PHENYL-1,2-EPOXYPROPANE [J].

BESSE, P ;

RENARD, MF ;

VESCHAMBRE, H .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1249-1268

[7]

Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871

[8] ENANTIOMERIC ANALYSIS IN A POLYPEPTIDE LYOTROPIC LIQUID-CRYSTAL BY DEUTERIUM NMR [J].

CANET, I ;

COURTIEU, J ;

LOEWENSTEIN, A ;

MEDDOUR, A ;

PECHINE, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6520-6526

[9] Acetyl-d(3) chloride: A convenient nonchiral derivatizing agent (NCDA) for a facile enantiomeric excess determination of amines through deuterium NMR [J].

Canet, JL ;

Canet, I ;

Courtieu, J ;

DaSilva, S ;

Gelas, J ;

Troin, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9035-9037

[10] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

← 1 2 3 4 5 →