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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: vladuic.edu

A. Trofimov, V. Gevorgyan, Org. Lett., 2009, 11, 253-255.

DOI: 10.1021/ol8026522 (free Supporting Information)


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