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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: 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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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.

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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