Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Osamu Kitagawa, Masashi Takahashi, Masatoshi Yoshikawa, Takeo Taguchi

Research output: Contribution to journalArticle

86 Citations (Scopus)

Abstract

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).

Original languageEnglish
Pages (from-to)3676-3677
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number11
DOIs
Publication statusPublished - 2005 Mar 23
Externally publishedYes

ASJC Scopus subject areas

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

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