Iron catalyzed asymmetric oxyamination of olefins.
The regioselective and enantioselective oxyamination of alkenes with N-sulfonyl oxaziridines is catalyzed by a novel iron(II) bis(oxazoline) complex. This process affords oxazolidine products that can be easily manipulated to yield highly enantioenriched free amino alcohols. The regioselectivity of this process is complementary to that obtained from the analogous copper(II)-catalyzed reaction. Thus, both regioisomers of enantioenriched 1,2-aminoalcohols can be obtained using oxaziridine-mediated oxyamination reactions, and the overall sense of regiochemistry can be controlled using the appropriate choice of inexpensive first-row transition metal catalyst.
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Kevin S
KS
Williamson
Tehshik P
TP
Yoon
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D005296:Ferrous Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D001388:Aziridines; D005296:Ferrous Compounds; D010080:Oxazoles