Stereoselective synthesis of fluorinated β-aminoacids from ethyl trans-N-benzyl-3-trifluoromethylaziridine-2-carboxylate

被引：47

作者：

Davoli, P ^{[1
]}

Forni, A ^{[1
]}

Franciosi, C ^{[1
]}

Moretti, I ^{[1
]}

Prati, F ^{[1
]}

机构：

[1] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(99)00246-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

trans-N-Benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtainable in enantiopure forms by CAL-catalysed enzymatic resolution, allowed the regio- and stereoselective synthesis of chiral fluorinated anti-alpha-functionalised-beta-aminoacids, such as trifluoroisoserinates or trifluoro-beta-alanine, and trans-3-halo- or 3-hydroxy-beta-lactams. Starting from the enantiomerically pure methyl analogue of the title compound, 2c, pure enantiomers of trifluoroisoserine can be obtained in high overall chemical yield. Absolute configurations of optically active beta-aminoacids were determined by chemical correlation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2361 / 2371

页数：11

共 17 条

[1] Diastereoselective synthesis of the nonracemic methyl syn-(3-fluoroalkyl)isoserinates [J].