Bridged Biaryl Atropisomers by Organocatalyzed Kinetic Asymmetric Alcoholysis
We disclose herein an asymmetric synthesis of axially chiral oxazepine-containing bridged biaryls via CPA-catalyzed kinetic asymmetric alcoholysis. Control experiments showed that this CPA-catalyzed alcoholysis was reversible, and lowering the reaction temperature could almost suppress the reversible reaction, thus providing a series of axially chiral oxazepine-containing bridged biaryl compounds in good to excellent enantioselectivities. The gram-scale reactions and facile derivatizations of the enantioenriched products demonstrate the practical utility of this reaction.
Authors
- Jiaomeng Li (ORCID: https://orcid.org/0000-0001-8874-9806)
- Wei Yuan (ORCID: https://orcid.org/0000-0003-4577-4619)
- Liwen Wei
- Tianyi Wang (ORCID: https://orcid.org/0000-0002-4790-7668)
- Yi Fang Zhao (ORCID: https://orcid.org/0000-0002-4531-8632)
- Xing Yang (ORCID: https://orcid.org/0009-0002-3031-6746)
- Zhikang Wei
Institutions
- Hunan Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c02345
- Citations
- 11
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 2.75
Funders
- Education Department of Hunan Province
- National Natural Science Foundation of China
- Hunan Normal University
- Natural Science Foundation of Hunan Province
- Science and Technology Program of Hunan Province