Enantioselective aldehyde α-nitroalkylation via oxidative organocatalysis

Jonathan E. Wilson, Anthony D. Casarez, David W.C. MacMillan

Research output: Contribution to journalArticle

96 Scopus citations

Abstract

(Chemical Equation Presented) The first enantioselective organocatalytic α-nitroalkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl nitronate to produce a β-nitroaldehyde. Two methods, one that furnishes the syn β-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-α,β-disubstituted β-amino acids is presented.

Original languageEnglish (US)
Pages (from-to)11332-11334
Number of pages3
JournalJournal of the American Chemical Society
Volume131
Issue number32
DOIs
StatePublished - Aug 19 2009

All Science Journal Classification (ASJC) codes

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

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