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 › peer-review

23 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

Access to Document

10.1021/acs.joc.5b02387

Fingerprint Dive into the research topics of 'Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives'. Together they form a unique fingerprint.

Cite this

@article{ff6af30f1a2c4916ac4a286db405701e,

title = "Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives",

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.",

author = "Tomoaki Hirata and Isao Takahashi and Yuya Suzuki and Hiroaki Yoshida and Hiroshi Hasegawa and Osamu Kitagawa",

year = "2016",

month = jan,

day = "4",

doi = "10.1021/acs.joc.5b02387",

language = "English",

volume = "81",

pages = "318--323",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives

AU - Hirata, Tomoaki

AU - Takahashi, Isao

AU - Suzuki, Yuya

AU - Yoshida, Hiroaki

AU - Hasegawa, Hiroshi

AU - Kitagawa, Osamu

PY - 2016/1/4

Y1 - 2016/1/4

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84953775620&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84953775620&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b02387

DO - 10.1021/acs.joc.5b02387

M3 - Article

AN - SCOPUS:84953775620

VL - 81

SP - 318

EP - 323

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 1

ER -