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Title: Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols
Authors: Yeung, CT 
Chan, WTK 
Lo, WS 
Law, GL 
Wong, WT 
Issue Date: 2019
Source: Beilstein journal of nanotechnology, 2019, v. 15, p. 955-962
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
Publisher: Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Journal: Beilstein journal of nanotechnology 
EISSN: 1860-5397
DOI: 10.3762/bjoc.15.92
Rights: © 2019 Yeung et al. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The following publication Yeung, C.-T.; Chan, W. T. K.; Lo, W.-S.; Law, G.-L.; Wong, W.-T. Beilstein J. Org. Chem. 2019, 15, 955–962 is available at https://doi.org/10.3762/bjoc.15.92
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