Copper-Catalyzed Asymmetric Cloke–Wilson Rearrangement
Herein we describe the first transition-metal-catalyzed asymmetric Cloke-Wilson rearrangement through unprecedented propargylic alkenoxylation reaction with enol as the <i>O</i>-nucleophile. A set of new chiral PPBOX ligands was prepared to guarantee the high enantioselectivity of the transformation. A series of polysubstituted dihydrofuran skeletons bearing an alkyne unit was prepared in good yield and high enantioselectivity under very mild reaction conditions, and various downstream transformations were facilely conducted to access different chiral skeletons.
Authors
- Zhi‐Tao He (ORCID: https://orcid.org/0000-0003-2375-9557)
- Guo‐Qiang Lin
- Jun-Han Yu
Institutions
- Chinese Academy of Sciences (CN)
- ShanghaiTech University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Institute for Advanced Study (DE)
- State Key Laboratory of Chemical Engineering (CN)
- University of Chinese Academy of Sciences (CN)
- State Key Laboratory of Organometallic Chemistry
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-07
- DOI
- https://doi.org/10.1021/acs.orglett.5c00847
- Citations
- 5
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Science and Technology Commission of Shanghai Municipality
- Natural Science Foundation of Ningbo
- Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences