121365-50-2Relevant academic research and scientific papers
A simple and versatile re-catalyzed meyer-schuster rearrangement of propargylic alcohols to α,β-unsaturated carbonyl compounds
Stefanoni, Massimo,Luparia, Marco,Porta, Alessio,Zanoni, Giuseppe,Vidari, Giovanni
experimental part, p. 3940 - 3944 (2009/12/03)
The development of a general catalytic procedure for the rapid and efficient 1,3-rearrangement of free secondary and tertiary propargylic alcohols to the corresponding α,β-unsaturated carbonyl compounds using available [ReOCl3(OPPh3)-(SMe2)] complex, was reported. The reaction was carried out under neutral environmental conditions with no racemization of potentially enolizable stereocenters with virtually complete E stereoselectivity. The reaction under dimethoxyethane, proceeded at the lower rate than in THF, but with reduced by-products and the yield obtained were highly significant. The reaction was reported to increase constantly at the expense of the (Z)-isomer 2b, where the double bong isomerization was attributed to a catalytic effect of the rhenium complex. The resulted new version of Meyer-Schuster rearrangement will find enormous application in organic synthesis to develop one-pot multistep reaction sequences.
