Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Selective Ring-Opening Reaction of Epoxides with Sodium Borohydride in the Presence of Cyclodextrins in Aqueous Media
Ying HuMitsunari UnoAkira HaradaShigetoshi Takahashi
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1991 Volume 64 Issue 6 Pages 1884-1888

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Abstract

In the presence of cyclodextrins (CDs), the ring-opening reaction of styrene oxide with NaBH4 in aqueous media proceeded smoothly to give 1-phenylethanol with high selectivity of up to 94%, and kinetic resolution of the racemic epoxide was observed. Kinetic studies suggest the resolution based on the different reaction rates between two enantiomers included in the CD’s cavity. The reaction of epoxides such as 1,2-epoxyindan and 1,2-epoxy-3-phenylpropane are also affected by the addition of CDs to proceed smoothly with high regioselectivities.

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