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Tandem Wittig Rearrangement/Aldol Reactions for the Synthesis of Glycolate Aldols

Myra Beaudoin Bertrand and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, Email:

M. B. Bertrand, J. P. Wolfe, Org. Lett., 2006, 8, 4661-4663.

DOI: 10.1021/ol062016l


A tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters generates two carbon-carbon bonds and two contiguous stereocenters with excellent diastereoselectivity in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions.

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proposed mechanism

Key Words

Aldol Addition, Wittig Rearrangement, Rearrangements, Diols, Hydroxy Carboxylic Acids

ID: J54-Y2006-3120