Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Osamu Kitagawa; Masashi Takahashi; Masatoshi Yoshikawa; Takeo Taguchi

doi:10.1021/ja042216x

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Osamu Kitagawa, Masashi Takahashi, Masatoshi Yoshikawa, Takeo Taguchi

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81 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 language	English
Pages (from-to)	3676-3677
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	11
DOIs	https://doi.org/10.1021/ja042216x
Publication status	Published - 2005 Mar 23

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

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, 127(11), 3676-3677. https://doi.org/10.1021/ja042216x

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AU - Taguchi, Takeo

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AB - 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).

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10.1021/ja042216x