Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes
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- 11 March 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (13) , 4108-4109
- https://doi.org/10.1021/ja049562z
Abstract
The first direct enantioselective catalytic alpha-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 alpha-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 beta-chiral aldehydes is also described. Catalyst quantities of 5 mol % were generally employed in this study.Keywords
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