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Synthesis of 2-aza-3-oxatetracyclo [7. 3. 1. 17,11. 02,6]tetradecane derivatives by the 1,3-dipolar cycloaddition reaction of homoadamantane-incorporated nitrones with alkenes

✍ Scribed by Yang Yu; Masatomi Ohno; Shoji Eguchi; Takashi Kawai; Yukimasa Terada

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 440 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00236-6

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✦ Synopsis

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[7.3.1.1711.0z6]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.

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