Stereoselective synthesis of N-phenylsulfonyl substituted spiro-β-lactams

被引：18

作者：

Dalla Croce, P

La Rosa, C

机构：

[1] Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

[2] Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[3] Ctr CNR, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(99)00096-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A stereoselective synthesis of N-phenylsulfonyl substituted spiro-beta-lactams obtained from the N-(phenylmethylene)benzenesulfonamide and the ketene valence tautomer of the bicyclic mesoionic compounds derived from 4-hydroxy substituted N-acyl-L-prolines in the presence of acetic anhydride as the dehydrating agent is presented. The reaction of (2S,4R)-4-acetyloxy or benzoyloxy-N-acyl-proline with the above imine afforded a mixture of two diastereoisomeric spiro-beta-lactams with complete stereoselectivity for the spiro carbon. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1193 / 1199

页数：7

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