The direct and enantioselective organocatalytic α-oxidation of aldehydes

Sean P. Brown, Michael P. Brochu, Christopher J. Sinz, David W.C. MacMillan

Research output: Contribution to journalArticle

472 Scopus citations

Abstract

The first direct enantioselective catalytic α-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate α-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described.

Original languageEnglish (US)
Pages (from-to)10808-10809
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number36
DOIs
StatePublished - Sep 10 2003

All Science Journal Classification (ASJC) codes

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

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