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Silylene Transfer to Carbonyl Compounds and Subsequent Ireland−Claisen Rearrangements to Control Formation of Quaternary Carbon Stereocenters

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posted on 23.02.2005, 00:00 by Stacie A. Calad, K. A. Woerpel
In this communication, we demonstrate that silylene transfer to carbonyl compounds provides a new method for regio- and stereoselective enolate formation. Silylene transfer to a range of α,β-unsaturated esters under silver-catalyzed conditions proved to be a general method for the formation of oxasilacyclopentenes containing a cyclic silyl ketene acetal functionality. These oxasilacyclopentenes are useful synthetic intermediates that can undergo facile and selective Ireland−Claisen rearrangements and aldol addition reactions to provide products with multiple contiguous stereocenters and quaternary carbon centers.