REACTION OF CONJUGATED ENONES WITH tert-BUTYLDIMETHYLSILYL TRIFLATE AND INTRAMOLECULAR ANNELATION

Masataka Ihara; Yohhei Ishida; Keiichiro Fukumoto; Tetsuji Kametani

doi:10.1248/cpb.33.4102

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

REACTION OF CONJUGATED ENONES WITH tert-BUTYLDIMETHYLSILYL TRIFLATE AND INTRAMOLECULAR ANNELATION

Masataka Ihara, Yohhei Ishida, Keiichiro Fukumoto, Tetsuji Kametani

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Keywords: tricyclo [5.2.2.0^{1, 5}] undecene

JOURNAL FREE ACCESS

1985 Volume 33 Issue 9 Pages 4102-4105

DOI https://doi.org/10.1248/cpb.33.4102

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Abstract

Reaction of 2-cyclohexen-1-ones (3a-c) with tert-butyldimethylsilyl triflate and triethylamine gave selectively cross-conjugated dienol ethers (4a-c) except 3-methyl-2-cyclohexen-1-one (3d). Reaction of 6-(5-ethoxycarbonyl-3, 3-dimethyl-4-pentenyl-1)-2-cyclohexen-1-one (10) under the same reaction conditions gave rise to annelation affording to tricyclo [5.2.2.0^{1, 5}] undecenes (11) along with the throughconjugated dienol ether (12).

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