Single enantiomer epoxides by bromomandelation of prochiral alkenes.

J Org Chem

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.

Published: January 2007

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Article Abstract

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3248826PMC
http://dx.doi.org/10.1021/jo061818rDOI Listing

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