Highly enantioselective synthesis of atropisomeric anilide derivatives through catalytic asymmetric N-arylation: Conformational analysis and application to asymmetric enolate chemistry

Osamu Kitagawa, Masatoshi Yoshikawa, Hajime Tanabe, Tomofumi Morita, Masashi Takahashi, Yasuo Dobashi, Takeo Taguchi

研究成果査読

114 被引用数 (Scopus)

抄録

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation (aromatic amination) of various o-tert-butylanilides with p-iodonitrobenzene proceeds with high enantioselectivity (88-96% ee) to give atropisomeric N-(p-nitrophenyl)anilides having an N-C chiral axis in good yields. Atropisomeric anilide products highly prefer to exist as the E-rotamer which has trans-disposed o-tert-butylphenyl group and carbonyl oxygen. The application of the present catalytic enantioselective N-arylation to an intramolecular version gives atropisomeric lactam derivatives with high optical purity (92-98% ee). The reaction of the lithium enolate prepared from the atropisomeric anilide and lactam products with various alkyl halides gives α-alkylated products with high diastereoselectivity (diastereomer ratio = 13:1 to 46:1).

本文言語English
ページ(範囲)12923-12931
ページ数9
ジャーナルJournal of the American Chemical Society
128
39
DOI
出版ステータスPublished - 2006 10 4
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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