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: sharples
scripps.edu
Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett., 2000, 2, 2221-2223.
DOI: 10.1021/ol000098m
see article for more reactions
Abstract
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.
see article for more examples
Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates
B. Tao, G. Schlingloff, K. B. Sharpless, Tetrahedron Lett., 1998, 39, 2507-2510.
Key Words
Sharpless Oxyamination, Amino Acids, Amino Alcohols, Asymmetric reactions, Catalysis
ID: J54-Y2000-660
