Construction of contiguous tetrasubstituted carbon stereocenters by intramolecular crossed benzoin reactions catalyzed by N-heterocyclic carbene (NHC) organocatalyst

Tadashi Ema, Kumiko Akihara, Ryoko Obayashi, Takashi Sakai

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

Bicyclic compounds with two contiguous tetrasubstituted carbon stereocenters at bridgehead positions were synthesized by N-heterocyclic carbene (NHC)-catalyzed intramolecular crossed benzoin reactions of symmetrical compounds. This desymmetrization strategy was applied to asymmetric synthesis with chiral NHC organocatalysts. Transition-state models were proposed to explain the enantioselectivity. A tricyclic compound with three contiguous tetrasubstituted carbon stereocenters was synthesized by a stepwise strategy. The molecular structure and absolute configuration of the (+)-enantiomer of this tricyclic compound were determined by X-ray crystallographic analysis.

Original languageEnglish
Pages (from-to)3283-3290
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number17
DOIs
Publication statusPublished - Nov 26 2012

Keywords

  • N-heterocyclic carbene
  • asymmetric catalysis
  • benzoin reaction
  • organocatalysis
  • quaternary stereocenters

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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