Synthesis, enzymatic resolution and absolute configuration of ethyl trans-3-(trifluoromethyl)pyroglutamate

被引：20

作者：

Antolini, L

Forni, A

Moretti, I

Prati, F

Laurent, E

Gestmann, D

机构：

[1] UNIV MODENA, DIPARTIMENTO CHIM, I-41100 MODENA, ITALY

[2] UNIV LYON 1, CHIM ORGAN LAB 3, F-69622 VILLEURBANNE, FRANCE

[3] POLITECN MILAN, CNR, DIPARTIMENTO CHIM, I-20131 MILAN, ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 11期

关键词：

D O I：

10.1016/0957-4166(96)00432-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ethyl trans-3-(trifluoromethyl)pyroglutamate 1 is synthesized in excellent yield; racemic 1 is enzymatically resolved with alpha-chymotrypsin-catalyzed hydrolysis affording both the enantiomerically pure enantiomers. The absolute configuration is established by X-ray analysis of the corresponding trichloroethylester. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3309 / 3314

页数：6

共 10 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[2] 2-HYDROXY-3-PINANONE AS CHIRAL AUXILIARY IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

ELACHQAR, A ;

BOUMZEBRA, M ;

ROUMESTANT, ML ;

VIALLEFONT, P .

TETRAHEDRON, 1988, 44 (17) :5319-5332

[3]

FABER K, 1992, BIOTRANSFORMATIONS O

[4] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[5]

GESTMANN D, 1996, IN PRESS J FLUORINE

[6]

Kukhar VP., 1995, FLUORINE CONTAINING

[7] SYNTHESIS OF CHIRAL AND BIOACTIVE FLUOROORGANIC COMPOUNDS [J].

RESNATI, G .

TETRAHEDRON, 1993, 49 (42) :9385-9445

[8]

SHELDRICK G, 1993, SHELXL 93

[9] PHASE ANNEALING IN SHELX-90 - DIRECT METHODS FOR LARGER STRUCTURES [J].

SHELDRICK, GM .

ACTA CRYSTALLOGRAPHICA SECTION A, 1990, 46 :467-473

[10]

SIH CJ, 1989, TOP STEREOCHEM, V19, P63

← 1 →