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.
Demko
Z P
ZP
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Bartsch
M
M
Sharpless
K B
KB
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