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)]


Published in:
Chemistry - A European Journal, 7, 9, 1909-14
Year:
2001
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
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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