Abstract

Rapid metal-halogen exchange reactions have been used to initiate the stereoselective formation of transbicyclo[4.3.0]nonane and strained trans-bicyclo[3.3.0]octane derivatives through sequential intramolecular conjugate addition reactions. Stereoselectivity has been controlled in anionic olefin addition reactions as well as in corresponding radical cyclizations through control of acceptor olefin stereochemistry.

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