Bicyclo[3.3.1]nonanes as synthetic intermediates .19. Asymmetric cleavage of omega-azabicyclo[3.n.1]alkan-3-ones at the 'fork head'

被引：34

作者：

Momose, T ^{[1
]}

Toshima, M ^{[1
]}

Toyooka, N ^{[1
]}

Hirai, Y ^{[1
]}

Eugster, CH ^{[1
]}

机构：

[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 09期

关键词：

D O I：

10.1039/a607812e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric cleavage of omega-azabicyclo[3.n.1]alkan-3-ones was achieved by asymmetric deprotonation at the 'fork head' ketone system with Koga's chiral base and subsequent ozonolysis of the resulting chiral silyl enol ether to give the cis-alpha,alpha'-disubstituted piperidine, pyrrolidine and hexahydroazepine, respectively, in high enantiomeric excess.

引用

页码：1307 / 1313

页数：7

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