Investigation of a stereoselective co-mediated rearrangement reaction |
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Authors: | Carbery David R Reignier Serge Miller Neil D Adams Harry Harrity Joseph P A |
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Affiliation: | Department of Chemistry, University of Sheffield, Brook Hill, UK. |
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Abstract: | A stereocontrolled approach to alpha-alkyl beta-alkynyl cyclohexanones is reported through a Lewis acid mediated rearrangement reaction of enol ethers bearing an Co-alkyne moiety. The reaction proceeds with high levels of stereoselectivity in the presence of Ti- and B-Lewis acids to provide a range of alpha,beta-disubstituted cyclohexanones in high yield although the products are prone to epimerization at the alpha-position in the presence of the B-promoter system. The potential for an enantioselective variant of this process is outlined, and a rationale for the observed stereochemical trends and detailed structural analyses of the ketone products are described. |
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