Synthesis of optically active atropisomeric anilide derivatives and their application to asymmetric reaction

Osamu Kitagawa, T. Taguchi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

N-Substituted anilide derivatives bearing a large substitutent such as a tert-Bu group at the ortho-position have atropisomerism due to the high rotation barrier of the N-Ar bond and resist racemization. We have succeeded in the synthesis of such atropisomeric N-Ar amides, imides and lactams with high optically purity and definite absolute configuration, and the development of various asymmetric reactions using them. Furthermore, catalytic asymmetric reaction with such atropisomeric anilide as a chiral ligand is also described.

Original languageEnglish
Pages (from-to)680-688
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume59
Issue number7
Publication statusPublished - 2001
Externally publishedYes

Fingerprint

Anilides
Bearings (structural)
Imides
Derivatives
Lactams
Amides
Ligands

Keywords

  • Amide
  • Anilide
  • Asymmetric catalyst
  • Asymmetric reaction
  • Atropisomerism
  • Chiral ligand
  • Imide
  • Lactam
  • Optically active

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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AU - Taguchi, T.

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AB - N-Substituted anilide derivatives bearing a large substitutent such as a tert-Bu group at the ortho-position have atropisomerism due to the high rotation barrier of the N-Ar bond and resist racemization. We have succeeded in the synthesis of such atropisomeric N-Ar amides, imides and lactams with high optically purity and definite absolute configuration, and the development of various asymmetric reactions using them. Furthermore, catalytic asymmetric reaction with such atropisomeric anilide as a chiral ligand is also described.

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