Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams

被引：11
|
作者：
Cremonesi, Giuseppe [1 ]
Croce, Piero Dalla [2 ,3 ]
Fontana, Francesco [2 ,3 ]
La Rosa, Concetta [1 ]
机构：
[1] Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[3] ISTM, CNR, I-20133 Milan, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 05期
关键词：
D O I：
10.1016/j.tetasy.2008.02.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-beta-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-beta-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：554 / 561
页数：8
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