Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines

被引：18
|
作者：
Cremonesi, G
Dalla Croce, P
Fontana, F
Forni, A
La Rosa, C
机构：
[1] Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
[2] Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[3] CNR, ISTM, I-20133 Milan, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 20期
关键词：
D O I：
10.1016/j.tetasy.2005.08.054
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：3371 / 3379
页数：9
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