Synthesis of enantiopure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2-d][1,4] oxazepine-9a(7H)-carboxylate by carbenoid/ylide/Stevens-[1,2]-shift with ring enlargement

被引：18

作者：

Chelucci, G

Saba, A

Valenti, R

Bacchi, A

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

[2] Dipartimento Chim Gen & Inorgan Chim Analit Chim, I-43100 Parma, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(00)00312-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2d][1,4]oxazepine-9a(7H)-carboxylate were obtained by Cu(II)-catalyzed decomposition of an alpha-diazo carbonyl tethered to a chiral morpholinone. The reaction occurred with moderate diastereoselectivity but with complete enantioselectivity through the carbenoid/spiro-[5,6]-ammonium ylide/Stevens-[1,2]-shift with ring enlargement sequence. (C) 2000 Published by Elsevier Science Ltd.

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页码：3449 / 3453

页数：5

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