The enantioselective organocatalytic 1,4-addition of electron-rich benzenes to α,β-unsaturated aldehydes

Nick A. Paras, David W.C. MacMillan

Research output: Contribution to journalArticle

293 Scopus citations

Abstract

The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and medicinal agent synthesis. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to unsaturated aldehydes. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 10 mol % were generally employed in this study, successful alkylations conducted with catalyst loadings as low as 1 mol % are described.

Original languageEnglish (US)
Pages (from-to)7894-7895
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number27
DOIs
StatePublished - Jul 10 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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