Rhodium carboxylate catalyzed decomposition of vinyldiazoacetates in the presence of heterodienes: Enantioselective synthesis of the 6-azabicyclo[3.2.2]nonane and 6-azabicyclo[3.2.2]nonanone ring systems

被引：30

作者：

Davies, HML ^{[1
]}

Hodges, LM ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 16期

关键词：

D O I：

10.1021/jo025697g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dirhodium. tetracarboxylate catalyzed decomposition of vinyldiazoacetates in the presence of N-phenoxycarbonyl protected 1,2-dihydropyridines or 1-methyl-2-pyridones is a direct method for the construction of the 6-azabicyclo[3.2.2]nonane ring system. The [3 + 4] cycloaddition occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction is possible in these transformations either by using (S)-lactate methyl ester as a chiral auxiliary or dirhodium tetraprolinates as chiral catalysts.

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页码：5683 / 5689

页数：7

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