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

doi:10.3762/bjoc.15.92

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

Beilstein J Org Chem. 2019 Apr 18:15:955-962. doi: 10.3762/bjoc.15.92. eCollection 2019.

Authors

Chi-Tung Yeung^{1

2}, Wesley Ting Kwok Chan², Wai-Sum Lo^{1

2}, Ga-Lai Law^{1

2}, Wing-Tak Wong^{1

2}

Affiliations

¹ The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen, PR China.
² State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.

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.

Keywords: asymmetric organocatalysis; axial chirality; biaryls; hydrogen bond; oxo-Diels–Alder reaction.