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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:

Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett., 2000, 2, 2221-2223.

DOI: 10.1021/ol000098m

see article for more reactions


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