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Stereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1,2-Amino Alcohols

Amanda F. Ward and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email: jpwolfeumich.edu

A. F. Ward, J. P. Wolfe, Org. Lett., 2011, 13, 4728-4731.

DOI: 10.1021/ol2020048 (free Supporting Information)


Abstract

A stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol derivatives. The transformations generate cis-disubstituted products with good to excellent diastereoselectivity, and enantiomerically enriched substrates are converted without loss of optical purity.

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Key Words

Oxazolidines


ID: J54-Y2011-2570