Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N-C chiral axis

Isao Takahashi, Fumika Morita, Shunsuke Kusagaya, Haruhiko Fukaya, Osamu Kitagawa

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

In the presence of an (R)-MOP-Pd2(dba)3 catalyst, the reaction of ortho-tert-butylaniline with 2-bromophenyl arylethynyl ketone proceeded via a tandem amination (1,4-addition of aniline to an ynone and subsequent intramolecular Buchwald-Hartwig amination) to afford axially chiral N-(2-tert-butylphenyl)-2-aryl-4-quinolinone derivatives with moderate enantioselectivity (up to 72% ee).

Original languageEnglish
Pages (from-to)1657-1662
Number of pages6
JournalTetrahedron Asymmetry
Volume23
Issue number24
DOIs
Publication statusPublished - 2012 Dec 31

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4-Quinolones
Amination
aniline
ketones
Derivatives
catalysts
Enantioselectivity
Aniline
synthesis
Ketones
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N-C chiral axis. / Takahashi, Isao; Morita, Fumika; Kusagaya, Shunsuke; Fukaya, Haruhiko; Kitagawa, Osamu.

In: Tetrahedron Asymmetry, Vol. 23, No. 24, 31.12.2012, p. 1657-1662.

Research output: Contribution to journalArticle

Takahashi, Isao ; Morita, Fumika ; Kusagaya, Shunsuke ; Fukaya, Haruhiko ; Kitagawa, Osamu. / Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N-C chiral axis. In: Tetrahedron Asymmetry. 2012 ; Vol. 23, No. 24. pp. 1657-1662.
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