Primary amides. A general nitrogen source for catalytic asymmetric aminohydroxylation of olefins.
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.
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Z P
ZP
Demko
M
M
Bartsch
K B
KB
Sharpless
D000081:Acetamides / Q000737:chemistry / Q000378:metabolism; D000475:Alkenes / Q000737:chemistry* / Q000378:metabolism*; D000577:Amides / Q000737:chemistry* / Q000378:metabolism*; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism; D006900:Hydroxylation; D009584:Nitrogen / Q000378:metabolism*; D013237:Stereoisomerism; D013890:Thiourea / Q000378:metabolism
D000081:Acetamides; D000475:Alkenes; D000577:Amides; D002934:Cinnamates; C016272:N-bromoacetamide; D013890:Thiourea; D009584:Nitrogen