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Letter

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

Supporting Info

Myra Beaudoin Bertrand and John P. Wolfe*

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

Org. Lett., 2006, 8 (20), pp 4661–4663

DOI: 10.1021/ol062016l

Publication Date (Web): August 26, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jpwolfe@umich.edu

Abstract

A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon−carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions that do not require the use of a strong base, and the 1,2-diol products are obtained in good yield with excellent diastereoselectivity (>20:1).

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Published In Issue September 28, 2006
Received August 15, 2006

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantioselective Intramolecular Friedel−Crafts-Type α-Arylation of Aldehydes

Recent Advances in Efficient and Selective Synthesis of Di-, Tri-, and Tetrasubstituted Alkenes via Pd-Catalyzed Alkenylation−Carbonyl Olefination Synergy

Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen

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