Rate Acceleration of Anionic Oxy-Cope Rearrangements Induced by an Additional Unsaturation

In sharp contrast to their isopropyl counterparts, a variety of (Z)-isopropenyl tertiary bicyclo[2.2.2]octenols undergo facile anionic oxy-Cope rearrangements allowing the stereoselective incorporation of an isopropenyl group into polycyclic skeletons such as the tricyclic system of vinigrol, bicycl...

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Bibliographic Details
Published in:Organic letters 2003-10, Vol.5 (20), p.3631-3634
Main Authors: Gentric, Lionel, Hanna, Issam, Huboux, Alexandre, Zaghdoudi, Rachida
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:In sharp contrast to their isopropyl counterparts, a variety of (Z)-isopropenyl tertiary bicyclo[2.2.2]octenols undergo facile anionic oxy-Cope rearrangements allowing the stereoselective incorporation of an isopropenyl group into polycyclic skeletons such as the tricyclic system of vinigrol, bicyclo[5.3.1]undecane, and cis-decalin frameworks. This rate acceleration is probably due to the stabilization of the transition state by the additional unsaturation on the terminal position.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035283p