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Journal article

About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes

(Z)-omega-Trimethylsilyl-(omega-2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega-1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z)-omega-trimethylsilyl-(omega-2)-alkenals which, in the presence of trifluoroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylcyclohexanol (2), isopulegol (4), and bis(2-vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interference of a novel electrodynamic effect. [on SciFinder (R)]

    Note:

    Section de Chimie de l'Universite, Lausanne-Dorigny, Switzerland 0947-6539 FIELD Electronic Internat.Standard Doc. Number: Germany: Germany, Federal Republic of Journal; Article; (JOURNAL ARTICLE) English

    Reference

    • LSCO-ARTICLE-2001-002

    Record created on 2006-03-03, modified on 2016-08-08

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