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 journalArticle

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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.

LanguageEnglish
Pages318-323
Number of pages6
JournalJournal of Organic Chemistry
Volume81
Issue number1
DOIs
StatePublished - 2016 Jan 4

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Bearings (structural)
Amination
Enantioselectivity
Nitrogen
Derivatives
Atoms
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives. / Hirata, Tomoaki; Takahashi, Isao; Suzuki, Yuya; Yoshida, Hiroaki; Hasegawa, Hiroshi; Kitagawa, Osamu.

In: Journal of Organic Chemistry, Vol. 81, No. 1, 04.01.2016, p. 318-323.

Research output: Contribution to journalArticle

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, vol. 81, no. 1, pp. 318-323. DOI: 10.1021/acs.joc.5b02387
Hirata T, Takahashi I, Suzuki Y, Yoshida H, Hasegawa H, Kitagawa O. Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives. Journal of Organic Chemistry. 2016 Jan 4;81(1):318-323. Available from, DOI: 10.1021/acs.joc.5b02387
Hirata, Tomoaki ; Takahashi, Isao ; Suzuki, Yuya ; Yoshida, Hiroaki ; Hasegawa, Hiroshi ; Kitagawa, Osamu. / Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives. In: Journal of Organic Chemistry. 2016 ; Vol. 81, No. 1. pp. 318-323
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