title: About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes.
abstract: (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.
authors.affiliation: Section de Chimie de l'Université, Lausanne-Dorigny, Switzerland.
authors.forename: M
authors.initials: M
authors.lastname: Schlosser
authors.forename: L
authors.initials: L
authors.lastname: Franzini
authors.forename: C
authors.initials: C
authors.lastname: Bauer
authors.forename: F
authors.initials: F
authors.lastname: Leroux