Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes

Michael P. Brochu, Sean P. Brown, David W.C. MacMillan

Research output: Contribution to journalArticle

271 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4108-4109
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number13
DOIs
StatePublished - Apr 7 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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