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: Article査読

113 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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