A solution to the cyclic aldol problem
[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.
Baldwin
SW
Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham, North Carolina 27708, USA. baldwin@chem.duke.edu
Chen
P
Nikolic
N
Weinseimer
DC