A solution to the cyclic aldol problem |
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Authors: | Baldwin Chen Nikolic Weinseimer |
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Institution: | Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham, North Carolina 27708, USA. baldwin@chem.duke.edu |
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Abstract: | formula: see text] A protocol for achieving stereoselective aldol reactions with cyclic ketones is presented. In terms of yield, the process is particularly effective when a quaternary center at the alpha-carbon of the beta-hydroxy ketone product is created. The stereochemical outcome, anti or syn, is achieved by the Lewis acid-mediated ring expansion of stereochemically homogeneous epoxides in a reaction related to the pinacol rearrangement. |
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