SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TIN ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - A COMPARISON BETWEEN TITANIUM AND TIN ENOLATES

被引：21

作者：

ANNUNZIATA, R

BENAGLIA, M

CINQUINI, M

COZZI, F

RAIMONDI, L

机构：

[1] UNIV MILAN,CTR CNR,I-20133 MILAN,ITALY

[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)85649-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of tricthylamine to a mixture of 2-pyridylthioesters and SnCl4 or SnBr4 affords the corresponding tin(IV) enolates that add to imines to give beta-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.

引用

页码：5821 / 5828

页数：8

共 18 条

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