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
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
收藏
页码:5821 / 5828
页数:8
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