Stereoselective azide cycloaddition to chiral cyclopentanone enamines

被引：14

作者：

Fioravanti, S ^{[1
]}

Pellacani, L ^{[1
]}

Ricci, D ^{[1
]}

Tardella, PA ^{[1
]}

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM,I-00185 ROME,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(97)00239-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enamine derived from cyclopentanone and (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine added ethyl N-mesylazidoformimidate [N3C(OEt)NMs] and ethyl azidoformate (N3CO2Et) with high asymmetric induction (>95%), while the corresponding cyclohexanone enamine gave ring contraction products. With the same azides the cyclopentanone enamine, prepared from (S)-2-(methoxymethyl)pyrrolidine gave N-substituted alpha-amino cyclopentanones in moderate enantiomeric excess. (C) 1997 Elsevier Science Ltd.

引用

页码：2261 / 2266

页数：6

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