Single enantiomer epoxides by bromomandelation of prochiral alkenes.
A combination of mandelic acid and N-bromosuccinimide efficiently converts prochiral alkenes into a readily separable 1:1 mixture of the bromomandelates. The diastereomerically pure bromomandelates are then converted into a variety of enantiomerically pure products. Terminal alkenes are converted into enantiomerically pure epoxides. Cyclohexene is converted into enantiomerically pure cis-2-azidocyclohexanol and cis-2-phenylthiocyclohexanol.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. Taberdf@udel.edu
Liang
Jiang-lin
JL
D000475:Alkenes / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry; D003511:Cyclohexanols / Q000138:chemical synthesis; D053138:Cyclohexenes / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008333:Mandelic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D003511:Cyclohexanols; D053138:Cyclohexenes; D004852:Epoxy Compounds; D008333:Mandelic Acids; C052568:cyclohexene; D001974:Bromosuccinimide; C037938:mandelic acid