[2+2] Cycloaddition reactions of imines with cyclic ketenes:: Synthesis of 1,3-thiazolidine derived spiro-β-lactams and their transformations

被引：14
|
作者：
Cremonesi, G
Dalla Croce, P
La Rosa, C
机构：
[1] Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
[2] CNR, ISTM, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
来源：
HELVETICA CHIMICA ACTA | 2005年 / 88卷 / 06期
关键词：
D O I：
10.1002/hlca.200590125
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unsymmetric cyclic ketenes were generated from N-acyl-1,3-thiazolidine-2-carboxylic acids la-c by means of Mukaiyama's reagent, and then reacted with imines 2a - c to the new, isomeric spiro-beta-lactams 3 and 4 via [2+2] cycloaddition (Staudinger ketene-imine reaction; Scheme 1). The reactions were stereoselective (Table 1) and mainly afforded the spiro-beta-lactams with a relative trans configuration. The spiro-beta-lactams could be transformed into the corresponding monocyclic beta-lactams by means of thiazolidine ring opening or into substituted thiazolidines via hydrolysis of the beta-lactam ring.
引用
收藏
页码：1580 / 1588
页数：9
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