Iron-catalyzed aminohydroxylation of olefins.
We have discovered that N-sulfonyl oxaziridines react with a broad range of olefins in the presence of iron salts to afford 1,3-oxazolidines. This process provides access to 1,2-aminoalcohols with the opposite sense of regioselectivity produced from the copper-catalyzed oxyamination previously reported by our laboratories. Thus, either regioisomeric form of 1,2-aminoalcohols can easily be obtained from the reaction of oxaziridines with olefins, and the sense of regioselectivity can be controlled by the appropriate choice of inexpensive, nontoxic, first-row transition-metal catalyst.
Williamson
Kevin S
KS
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Yoon
Tehshik P
TP
D000475:Alkenes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005290:Ferric Compounds / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000605:Amino Alcohols; D005290:Ferric Compounds