Dynamic Kinetic Asymmetric Transformations of β‐Stereogenic α‐Ketoesters by Direct Aldolization |
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Authors: | Michael T Corbett Prof?Dr Jeffrey S Johnson |
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Institution: | Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599 (USA) http://www.unc.edu/jsjgroup/Home.html |
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Abstract: | Dynamic kinetic asymmetric transformations (DyKAT) of racemic β‐bromo‐α‐keto esters by direct aldolization of nitromethane and acetone provide access to fully substituted α‐glycolic acid derivatives bearing a β‐stereocenter. The aldol adducts are obtained in excellent yield with high relative and absolute stereocontrol under mild reaction conditions. Mechanistic studies determined that the reactions proceed through a facile catalyst‐mediated racemization of the β‐bromo‐α‐keto esters under a DyKAT Type I manifold. |
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Keywords: | acetone aldol reaction DyKAT Henry reaction α ‐ketoesters organocatalysis |
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