Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols

Chi Tung Yeung, Wesley Ting Kwok Chan, Wai Sum Lo, Ga Lai Law, Wing Tak Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF3 substituents, shows the formation of a monomeric structure. Diols 1-6 were found to be active organocatalysts in oxo-Diels-Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.

Original languageEnglish
Pages (from-to)955-962
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 2019

Keywords

  • Asymmetric organocatalysis
  • Axial chirality
  • Biaryls
  • Hydrogen bond
  • Oxo-Diels-Alder reaction

ASJC Scopus subject areas

  • Organic Chemistry

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