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

1 Citation (Scopus)

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

Fingerprint

Bearings (structural)
Quinazolinones
Chirality
Alkylation
Derivatives
Temperature

Keywords

  • alkylation
  • axial chirality
  • diastereoselectivity
  • quinazolinones

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent",
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{\%}).",
keywords = "alkylation, axial chirality, diastereoselectivity, quinazolinones",
author = "Mizuki Matsuoka and Asumi Iida and Osamu Kitagawa",
year = "2018",
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day = "29",
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language = "English",
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T1 - α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups

T2 - Relation between Diastereoselectivity and the ortho -Substituent

AU - Matsuoka, Mizuki

AU - Iida, Asumi

AU - Kitagawa, Osamu

PY - 2018/5/29

Y1 - 2018/5/29

N2 - 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%).

AB - 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%).

KW - alkylation

KW - axial chirality

KW - diastereoselectivity

KW - quinazolinones

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