Highly diastereo- and enantioselective additions of homoenolates to nitrones catalyzed by N-heterocyclic carbenes

Eric M. Phillips, Troy E. Reynolds, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

147 Scopus citations

Abstract

The diastereo- and enantioselective addition of N-heterocyclic carbene-generated homoenolates to nitrones is reported. This formal [3 + 3] addition of α,β-unsaturated aldehydes and nitrones generates unusual morpholinone heterocycles which are converted into γ-hydroxy amino esters by addition of methanol to the reaction. The use of a chiral N-heterocyclic carbene (NHC) as the catalyst provides the amino esters in high diastereoselectivity (up to 20:1 dr) and enantioselectivity (up to 94%). The process accommodates α,β-unsaturated aldehydes with β-alkyl and β-aryl substituents. The γ-hydroxy amino esters can be converted to optically enriched γ-lactams by a two-step procedure involving mild reduction of the N-O bond and acid-catalyzed amide formation.

Original languageEnglish (US)
Pages (from-to)2416-2417
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number8
DOIs
StatePublished - Feb 27 2008

ASJC Scopus subject areas

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

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