SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - INFLUENCE OF THE IMINE STRUCTURE ON THE TRANS/CIS STEREOSELECTIVITY

被引：23

作者：

ANNUNZIATA, R ^{[1
]}

BENAGLIA, M ^{[1
]}

CINQUINI, M ^{[1
]}

COZZI, F ^{[1
]}

PONZINI, F ^{[1
]}

RAIMONDI, L ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)87005-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords beta-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans p-lactams, while sterically non-requiring or chelating groups favour the formation of the cia-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.

引用

页码：2939 / 2948

页数：10

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