Stereoselective epoxidation of 3‐ trans ‐benzylideneisoborneol | Zendy

Sanghvi Y. S. | Zendy; Rao A. S. | Zendy

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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 ).

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