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

Research output: Contribution to journal › Article › peer-review

87 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
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja042216x

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title = "Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction",

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).",

author = "Osamu Kitagawa and Masashi Takahashi and Masatoshi Yoshikawa and Takeo Taguchi",

year = "2005",

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doi = "10.1021/ja042216x",

language = "English",

volume = "127",

pages = "3676--3677",

journal = "Journal of the American Chemical Society",

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T1 - Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

AU - Kitagawa, Osamu

AU - Takahashi, Masashi

AU - Yoshikawa, Masatoshi

AU - Taguchi, Takeo

PY - 2005/3/23

Y1 - 2005/3/23

N2 - 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).

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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