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Stereoselective epoxidation of 3‐ trans ‐benzylideneisoborneol
Author(s) -
Sanghvi Y. S.,
Rao A. S.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210209
Subject(s) - chemistry , stereoselectivity , catalysis , alcohol , oxide , cis–trans isomerism , epoxide , medicinal chemistry , organic chemistry , stereochemistry
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 ).