α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent

Mizuki Matsuoka, Asumi Iida, Osamu Kitagawa

Research output: Contribution to journalArticle

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Abstract

2-Ethylquinazolin-4-one derivatives bearing various ortho -substituted phenyl groups were revealed to possess a stable C–N axially chiral structure at ambient temperature. The reactions of alkyl halides with the anionic species prepared from these quinazolinones were systematically explored. The α-alkylation reactions proceeded with diastereoselectivities ranging from 1:1 to >50:1, depending upon the steric bulk of the ortho -substituent, to afford products having the elements of axial and central chirality in high yields (85–98%).

Original languageEnglish
JournalSynlett
DOIs
Publication statusAccepted/In press - 2018 May 29

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Keywords

  • alkylation
  • axial chirality
  • diastereoselectivity
  • quinazolinones

ASJC Scopus subject areas

  • Organic Chemistry

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