Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

Motohiro Hirai; Shumpei Terada; Hiroaki Yoshida; Kenki Ebine; Tomoaki Hirata; Osamu Kitagawa

doi:10.1021/acs.orglett.6b02865

Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

Motohiro Hirai, Shumpei Terada, Hiroaki Yoshida, Kenki Ebine, Tomoaki Hirata, Osamu Kitagawa

研究成果: Article › 査読

46 被引用数 (Scopus)

抄録

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)₂ catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH₄ gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R²) at the C4′position, amount of NaBH₄, and reaction temperature.

本文言語	English
ページ（範囲）	5700-5703
ページ数	4
ジャーナル	Organic Letters
巻	18
号	21
DOI	https://doi.org/10.1021/acs.orglett.6b02865
出版ステータス	Published - 2016 11月 4

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.6b02865

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引用スタイル

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abstract = "In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R2) at the C4′position, amount of NaBH4, and reaction temperature.",

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AU - Yoshida, Hiroaki

AU - Ebine, Kenki

AU - Hirata, Tomoaki

AU - Kitagawa, Osamu

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