Primary Amides. A General Nitrogen Source for Catalytic Asymmetric Aminohydroxylation of Olefins
Zachary P. Demko, Michael Bartsch and K. Barry Sharpless*
*Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, Email: sharplesscripps.edu
Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett., 2000, 2, 2221-2223.
DOI: 10.1021/ol000098m (free Supporting Information)
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N-Bromo,N-lithio salts of primary carboxamides are efficient nitrogen sources for catalytic asymmetric aminohydroxylation of olefins, behaving much like the parent N-bromoacetamide in these reactions. α-Chloro-N-bromoacetamide is a particularly interesting nitrogen source, as it can be easily deprotected by treatment with thiourea.
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B. Tao, G. Schlingloff, K. B. Sharpless, Tetrahedron Lett., 1998, 39, 2507-2510.