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Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion |
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| Authors: | Dr. Seitaro Koshino Prof. Dr. Tohru Taniguchi Prof. Dr. Kenji Monde Prof. Dr. Eunsang Kwon Prof. Dr. Yujiro Hayashi |
| Affiliation: | 1. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578 Japan;2. Frontier Research Center of Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Sapporo, 001-0021 Japan;3. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 Japan |
| Abstract: | 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. |
| Keywords: | axial chirality chirality conversion enantiodivergent synthesis organocatalysis synthetic methods |