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.
Schlosser
M
M
Section de Chimie de l'Université, Lausanne-Dorigny, Switzerland.
Franzini
L
L
Bauer
C
C
Leroux
F
F