Memory of chirality in the stereoselective synthesis of β-lactams:: importance of the starting amino acid derivative

被引：29

作者：

Bonache, MA

Gerona-Navarro, G

García-Aparicio, C

Alías, M

Martín-Martínez, M

García-López, MT

López, P

Cativiela, C

González-Muñiz, R

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

[2] Univ Zaragoza, CSIC, ICMA, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(03)00398-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselectivity of the base-promoted cyclization of N-alkyl-N-chloroacetyl amino acid derivatives to beta-lactams is dependent on the substituents on the starting material. While Bu-t esters are preferred over Me esters, and N-Bzl-, N-Pmb, N-Nph and N-Mom groups gave similar e.e. values, only amino acid derivatives with branched side-chains at the gamma-position were able to show a good memory of chirality. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：2161 / 2169

页数：9

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