Intramolecular conjugate addition reactions of amines and carbamates to 2,5-cyclohexadien-1-ones: Stereoselective synthesis of perhydroindoles

被引：27

作者：

Bland, D ^{[1
]}

Chambournier, G ^{[1
]}

Dragan, V ^{[1
]}

Hart, DJ ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(99)00455-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular conjugate addition reactions of 4,4-disubstituted-2,5-cyclohexadien-1-ones are described within the context of possible approaches to manzamine A. Amine 4 provided tricycle 6, with improper relative stereochemistry for use in an approach to manzamine A. Carbamates 25 and 38 gave perhydroindoles 26 and 28b under conditions of thermodynamic control, respectively, with the proper relative stereochemistry required for manzamine A. Carbamate 25 Rave diastereomeric perhydroindole 27 under conditions of thermodynamic control. (C) 1999 Elsevier Science Ltd. AII rights reserved.

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页码：8953 / 8966

页数：14

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