Stereospecific synthesis of dienones via a torquoselective retro-Nazarov reaction.
[reaction: see text] Enol ethers are cleaved via a three-step sequence involving cycloaddition with dichloroketene, ring expansion with diazomethane, and a base-mediated retro-Nazarov reaction. The latter conrotatory process proceeds torquoselectively and stereospecifically in accord with theoretical predictions.
Harmata
Michael
M
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. harmatam@missouri.edu
Lee
Dong Reyoul
DR
Barnes
Charles L
CL