Stereoselective epoxidation of 3-trans-benzylideneisoborneol |
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| Authors: | Y S Sanghvi A S Rao |
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| Institution: | National Chemical Laboratory, POONA-411008, India
Communication number 3321 from the National Chemical Laboratory. |
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| Abstract: | 2-Benzylidenecyclopentanol ( 2 ) can be epoxidized stereoselectively to furnish 2-trans-benzylidene-1β-hydroxycyclopentane β-oxide ( 4 ) with either t-butyl hydroperoxide in the presence of vanadium catalyst or m-chloroperoxybenzoic acid. Epoxidation of 3-trans-benzylideneisoborneol ( 10 ) with t-butyl hydroperoxidevanadium catalyst furnishes stereoselectively 3-trans-benzylideneisoborneol exo-oxide ( 11 ) whereas epoxidation of alcohol 10 with m-chloroperoxybenzoic acid furnishes stereoselectively 3-trans-benzylideneisoborneol endo-oxide ( 14 ). |
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