Enantioselective organocatalytic amine conjugate addition

Young K. Chen, Masanori Yoshida, David W.C. MacMillan

Research output: Contribution to journalArticle

248 Scopus citations

Abstract

The first enantioselective organocatalytic amine conjugate addition has been successfully developed. The application of LUMO-lowering iminium catalysis has enabled the highly chemo- and enantioselective 1,4-addition of a rationally designed N-silyloxycarbamate nucleophile (HOMO-raised) to α,β-unsaturated aldehydes. Imidazolidinone 2•pTSA was found to catalyze the addition of various orthogonally N-protected silyloxycarbamate nucleophiles to a range of α,β-unsaturated aldehydes, affording synthetically useful β-amino aldehyde intermediates. The synthetic utility of the protocol was demonstrated in the rapid synthesis of enantioenriched β-amino acids in one operation and 1,3-amino alcohol derivatives in three operations.

Original languageEnglish (US)
Pages (from-to)9328-9329
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number29
DOIs
StatePublished - Jul 26 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

Fingerprint Dive into the research topics of 'Enantioselective organocatalytic amine conjugate addition'. Together they form a unique fingerprint.

  • Cite this