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

21 引用 (Scopus)

抜粋

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.

元の言語English
ページ(範囲)5700-5703
ページ数4
ジャーナルOrganic Letters
18
発行部数21
DOI
出版物ステータスPublished - 2016 11 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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