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)
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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B. R. Rosen, J. E. Ney, J. P. Wolfe, J. Org. Chem., 2010, 75, 2756-2759.