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Chemoselective allylic addition of allyltrichlorosilane to α-oxocarboxylic acids: synthesis of tertiary α-hydroxy carboxylic acids

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
23
Identifiers
DOI: 10.1016/s0040-4039(00)00692-4

Abstract

Abstract Allyltrichlorosilane can add to α-oxocarboxylic acids in the presence of DMF and HMPA. The α-carboxylic substituent exerts a remarkable neighboring group effect on the reaction. The reaction presumably proceeds in an intramolecular fashion through a ‘rigid’ bicyclic transition state assembly involving a hypervalent silicate species, which produces the chemoselectivity approaching 100%.

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