Cyclization and rearrangement of 4-(2-methyloxiranyl)-β-lactams promoted by titanocene dichloride/Zn0

被引：26

作者：

Anaya, J ^{[1
]}

Fernádez-Mateos, A ^{[1
]}

Grande, M ^{[1
]}

Martiáñez, J ^{[1
]}

Ruano, G ^{[1
]}

Rubio-González, MR ^{[1
]}

机构：

[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

TETRAHEDRON | 2003年 / 59卷 / 02期

关键词：

epoxy-beta-lactams; carbapenam; tribactam; titanocene; ring expansion;

D O I：

10.1016/S0040-4020(02)01459-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure epoxyalkene-2-azetidinones derived from D-glucosamine by Staudinger reaction gave on treatment for 2 h with titanoncene (III) monochloride generated in situ, bicyclic and tricyclic beta-lactams with high regio and stereo-selectivity but with low conversion. For extended reaction times (15-22 h) a rearranged five-membered ring imide was the main reaction product together with the tribactam. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：241 / 248

页数：8

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