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

doi:10.1055/s-0037-1610110

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 journal › Article

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 language	English
Journal	Synlett
DOIs	https://doi.org/10.1055/s-0037-1610110
Publication status	Accepted/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

Matsuoka, M., Iida, A., & Kitagawa, O. (Accepted/In press). α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent. Synlett. https://doi.org/10.1055/s-0037-1610110

α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups : Relation between Diastereoselectivity and the ortho -Substituent. / Matsuoka, Mizuki; Iida, Asumi; Kitagawa, Osamu.

In: Synlett, 29.05.2018.

Research output: Contribution to journal › Article

Matsuoka, M, Iida, A & Kitagawa, O 2018, 'α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent', Synlett. https://doi.org/10.1055/s-0037-1610110

Matsuoka M, Iida A, Kitagawa O. α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups: Relation between Diastereoselectivity and the ortho -Substituent. Synlett. 2018 May 29. https://doi.org/10.1055/s-0037-1610110

Matsuoka, Mizuki ; Iida, Asumi ; Kitagawa, Osamu. / α-Alkylation of N–C Axially Chiral Quinazolinone Derivatives Bearing Various ortho -Substituted Phenyl Groups : Relation between Diastereoselectivity and the ortho -Substituent. In: Synlett. 2018.

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10.1055/s-0037-1610110