Selective Ring-Opening Reaction of Epoxides with Sodium Borohydride in the Presence of Cyclodextrins in Aqueous Media
- 1 June 1991
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 64 (6), 1884-1888
- https://doi.org/10.1246/bcsj.64.1884
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.Keywords
This publication has 12 references indexed in Scilit:
- Inverse phase-transfer effect of cyclodextrins: oxidation reaction of benzyl alcohols by NaClO aqueous solutionJournal of Molecular Catalysis, 1990
- Asymmetric reduction of ketones with crystalline cyclodextrin complexes of amine-boranesThe Journal of Organic Chemistry, 1989
- Cyclodextrin-H O: A New System for Asymmetric EpoxidationSynthetic Communications, 1988
- .beta.-Cyclodextrin as a molecular reaction vessel: reactions of included phenylmethyldiazirineThe Journal of Organic Chemistry, 1988
- Convenient Method for the Chemoselective and Regioselective Reduction of Oxiranes with Sodium Borohydride in Single SolventHETEROCYCLES, 1988
- Asymmetric halogenation and hydrohalogenation of styrene in crystalline cyclodextrin complexesJournal of inclusion phenomena and molecular recognition in chemistry, 1987
- Selective syntheses using cyclodextrins as catalyst. 2. The para-oriented carboxylation of phenolsJournal of the American Chemical Society, 1984
- Asymmetric Catalytic Epoxydation by Means of CyclodextrinsSynthetic Communications, 1983
- Forty years of hydride reductionsTetrahedron, 1979
- Selective aromatic substitution by hydrophobic binding of a substrate to a simple cyclodextrin catalystBioorganic Chemistry, 1971