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.

引用

页码：3371 / 3379

页数：9

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