Sila-Morita-Baylis-Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem
Alexander Trofimov and Vladimir Gevorgyan*
*Department of Chemistry, University of Illinois at Chicago,
845 West Taylor Street, Chicago, Illinois 60607-7061, Email: vlad
uic.edu
A. Trofimov, V. Gevorgyan, Org. Lett., 2009, 11, 253-255.
DOI: 10.1021/ol8026522
Abstract
Under Morita-Baylis-Hillman (MBH) reaction conditions, arylvinyl ketones produce a mixture of dimerization products, whereas α-silylated vinyl ketones give Si-MBH adducts in good to excellent yields. This sila-MBH cascade reaction involves addition of phosphine catalyst to arylvinyl ketones, trapping of the forming β-silylenolate with aldehyde, followed by a 1,3-Brook rearrangement.
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proposed mechanism
Key Words
Baylis-Hillman Reaction, Brook Rearrangement
ID: J54-Y2009-0160
