Synthesis of 2-aza-3-oxatetracyclo [7. 3. 1. 1 7,11. 0 2,6]tetradecane derivatives by the 1,3-dipolar cycloaddition reaction of homoadamantane-incorporated nitrones with alkenes

The 1,3-dipolar cycloaddition reaction of homoadamantane-incorporated nitrones, 4-azahomoadamant-4-ene N-oxide ( 1) and 5-methyl-4-azahomoadamant-4-ene N-oxide ( 2), with various alkenes afforded 2-aza-3-oxatetracyclo[7.3.1.1 7,11.0 2,6]tetradecane derivatives as the 1:1 cycloadduct. The reaction sh...

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Bibliographic Details
Published in:Tetrahedron 1997-04, Vol.53 (15), p.5413-5422
Main Authors: Yu, Yang, Ohno, Masatomi, Eguchi, Shoji, Kawai, Takashi, Terada, Yukimasa
Format: Article
Language:English
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Summary:The 1,3-dipolar cycloaddition reaction of homoadamantane-incorporated nitrones, 4-azahomoadamant-4-ene N-oxide ( 1) and 5-methyl-4-azahomoadamant-4-ene N-oxide ( 2), with various alkenes afforded 2-aza-3-oxatetracyclo[7.3.1.1 7,11.0 2,6]tetradecane derivatives as the 1:1 cycloadduct. The reaction showed relatively low regio-and stereo-selectivities, however only the 5- endo adduct was not formed. This was rationalized by the steric effect in the course of reaction process on the basis of PM3 calculations of the transition state model. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00236-6