Asymmetric Synthesis of Biaryl Atropisomers Using an Organocatalyst-Mediated Domino Reaction as the Key Step

Yujiro Hayashi, Akira Takikawa, Seitaro Koshino, Keiichi Ishida

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A three-pot synthetic method that features the use of an organocatalyst as the key step was developed for the preparation of biaryl atropisomers. The first reaction is an asymmetric domino Michael–Henry reaction catalyzed by diphenylprolinol silyl ether to afford the substituted nitrocyclohexanecarbaldehyde with four stereogenic centers and one defined configuration of a stereogenic axis with excellent enantioselectivity. Removal of the central chirality from the domino products afforded biaryl atropisomers having axial chirality with excellent enantioselectivity.

Original languageEnglish
Pages (from-to)10319-10322
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number44
DOIs
Publication statusPublished - 2019 Aug 6

Keywords

  • asymmetric synthesis
  • atropisomers
  • axial chirality
  • organocatalyst
  • pot-economy

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Asymmetric Synthesis of Biaryl Atropisomers Using an Organocatalyst-Mediated Domino Reaction as the Key Step'. Together they form a unique fingerprint.

Cite this