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 journal › Article

79 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

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Anilides
Enantioselectivity
Lactams
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. / Kitagawa, Osamu; Takahashi, Masashi; Yoshikawa, Masatoshi; Taguchi, Takeo.

In: Journal of the American Chemical Society, Vol. 127, No. 11, 23.03.2005, p. 3676-3677.

Research output: Contribution to journal › Article

Kitagawa, O, Takahashi, M, Yoshikawa, M & Taguchi, T 2005, 'Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction', Journal of the American Chemical Society, vol. 127, no. 11, pp. 3676-3677. https://doi.org/10.1021/ja042216x
Kitagawa O, Takahashi M, Yoshikawa M, Taguchi T. Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. Journal of the American Chemical Society. 2005 Mar 23;127(11):3676-3677. https://doi.org/10.1021/ja042216x
Kitagawa, Osamu ; Takahashi, Masashi ; Yoshikawa, Masatoshi ; Taguchi, Takeo. / Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 11. pp. 3676-3677.
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