Synthesis of chiral bicyclo [2.2.2] oct-5-en-2-ones via an intramolecular alkylation reaction

Srikrishna, Adusumilli ; Veera Raghava Sharma, G. ; Danieldoss, Savariappan ; Hemamalini, Parthasarathy (1996) Synthesis of chiral bicyclo [2.2.2] oct-5-en-2-ones via an intramolecular alkylation reaction Journal of the Chemical Society, Perkin Transactions 1 (11). pp. 1305-1311. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1996...

Related URL: http://dx.doi.org/10.1039/P19960001305

Abstract

Generation of the thermodynamic dienolate of 9-bromocarvone derivatives 5,7 and 11 furnished the chiral bicyclo[2.2.2]octenones 6, 8 and 9 and 12 and 13 containing a bridgehead methyl group via an intramolecular alkylation reaction. In an analogous manner intramolecular alkylation reaction of the bromo enones 15a-e, obtained from carvone 2 by 1,3-alkylative enone transposition (→14) followed by a regiospecific bromoetherification reaction, furnished the bicyclo[2.2.2]oct-5-en-2-ones 16a-e and 17a-e.

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