Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives

Tomoaki Hirata; Isao Takahashi; Yuya Suzuki; Hiroaki Yoshida; Hiroshi Hasegawa; Osamu Kitagawa

doi:10.1021/acs.joc.5b02387

Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives

Tomoaki Hirata, Isao Takahashi, Yuya Suzuki, Hiroaki Yoshida, Hiroshi Hasegawa, Osamu Kitagawa

Research output: Contribution to journal › Article

18 Citations (Scopus)

Abstract

N-C axially chiral phenanthridin-6-one derivatives bearing various ortho-substituted phenyl groups on the nitrogen atom were enantioselectively prepared through (R)-DTBM-SEGPHOS-Pd(OAc)₂-catalyzed intramolecular Buchwald-Hartwig amination. The enantioselectivity strongly depended on solvents, bases, and reaction temperature as well as on the bulkiness of ortho-substituents.

Original language	English
Pages (from-to)	318-323
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	81
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.5b02387
Publication status	Published - 2016 Jan 4

ASJC Scopus subject areas

Organic Chemistry

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Hirata, T., Takahashi, I., Suzuki, Y., Yoshida, H., Hasegawa, H., & Kitagawa, O. (2016). Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives. Journal of Organic Chemistry, 81(1), 318-323. https://doi.org/10.1021/acs.joc.5b02387

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AU - Hasegawa, Hiroshi

AU - Kitagawa, Osamu

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