Terminal Alkyne-Ethylene Cross-Metathesis: Reaction of 1-Substituted Propargyl Esters at Elevated Ethylene Pressure.
Substituted propargylic esters, resistant to complete ethylene cross-metathesis at ambient pressure, underwent cross-metathesis with ethylene at elevated pressure (4 atm) to give 2-substituted butadienes in good to excellent yields. Enantioenriched propargylic acetates, obtained through enzymatic kinetic resolution of secondary propargyl alcohols, similarly underwent ethylene metathesis with retention of stereochemistry at the chiral center.
Smulik
JA
Department of Chemistry, State University of New York, Buffalo, New York 14260-3000.
Diver
ST