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Primary amides. A general nitrogen source for catalytic asymmetric aminohydroxylation of olefins
Z P Demko1, M Bartsch, K B Sharpless
1Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Organic Letters
|August 10, 2000
Abstract:
N-Bromo,N-lithio salts of primary carboxamides have been shown to be efficient nitrogen sources for catalytic asymmetric aminohydroxylation of olefins, behaving much like the parent N-bromoacetamide in these reactions. alpha-Chloro-N-bromoacetamide is a particularly interesting nitrogen source, as it is functionalized for further reaction, including easy deprotection by treatment with thiourea.