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Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes | Journal of the American Chemical Society
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    Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes
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    Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
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    Cite this: J. Am. Chem. Soc. 2004, 126, 13, 4108–4109
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    https://doi.org/10.1021/ja049562z
    Published March 11, 2004
    Copyright © 2004 American Chemical Society

    Abstract

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    The first direct enantioselective catalytic α-chlorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective chlorination of aldehydes to generate α-chloro aldehydes, an important chiral synthon for chemical and medicinal agent synthesis. The use of imidazolidinone 3 as the asymmetric catalyst has been found to mediate the halogenation of a large variety of aldehyde substrates with the perchlorinated quinone 1 serving as the electrophilic chlorinating reagent. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. The capacity of catalyst 3 to override the inherent bias of resident stereogenicity in the chlorination of enantiopure β-chiral aldehydes is also described. Catalyst quantities of 5 mol % were generally employed in this study.

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    Cite this: J. Am. Chem. Soc. 2004, 126, 13, 4108–4109
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    Published March 11, 2004
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