Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 63, Pages 15786-15794Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202102797
Keywords
axial chirality; chirality conversion; enantiodivergent synthesis; organocatalysis; synthetic methods
Categories
Funding
- JSPS KAKENHI [JP20H04801, JP19H05630, JP19K22178]
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A one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source, allowing for an enantiodivergent chirality conversion from central-to-axial chirality with excellent enantioselectivity. Both enantiomers of biaryls were obtained in a single reaction vessel, with a proposed plausible reaction mechanism for the enantiodivergence.
Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.
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