Direct catalytic asymmetric mannich-type reaction of benzyl isocyanide: Stereoselective synthesis of 1,2-diarylethylenediamines

Keiji Tamura, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A direct catalytic asymmetric Mannich-type reaction of benzyl isocyanide using a CuI catalyst and N-(diphenylthiophosphinoyl)imines was developed. The simultaneous activation strategy by soft-soft interaction was the key to promote the reaction using a weakly acidic pronucleophile, benzyl isocyanide. The spontaneous cyclization of the Mannich adduct afforded the corresponding enantioenriched imidazolines, which could be precursors for a variety of 1,2-diarylethylenediamines. Enantioenriched 4,5-diarylimidazolines were directly accessed by catalytic asymmetric C-C bond-forming reaction of benzyl isocyanide and N-(thiophosphinoyl)aldimines. The imidazolines were readily transformed into enantioenriched 1,2-diarylethylenediamines.

Original languageEnglish
Pages (from-to)3026-3031
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number14
DOIs
Publication statusPublished - 2015 May 1
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Chiral diamines
  • Imidazoline
  • Isocyanides
  • Mannich reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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