Citation: Yi-Fan Wang, Hao-Yun Yu, Hao Xu, Ya-Jie Wang, Xiaodi Yang, Yu-Hui Wang, Ping Tian, Guo-Qiang Lin. Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes[J]. Chinese Chemical Letters, ;2024, 35(9): 109520. doi: 10.1016/j.cclet.2024.109520 shu

Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes

The Research Center of Chiral Drugs, Shanghai Frontiers Science Center for TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

yuhuiwang@shutcm.edu.cn

tianping@shutcm.edu.cn

lingq@sioc.ac.cn

Received Date: 28 September 2023
Revised Date: 3 January 2024
Accepted Date: 10 January 2024
Available Online: 14 January 2024

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A rhodium(Ⅲ)-catalyzed hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes (1, 6-dienes) with triethylsilane is described, providing a series of cis-hydrobenzofurans, cis-hydroindoles, and cis-hydroindenes bearing silyl enol ether in good to excellent yields and excellent stereoselectivities. Additionally, the versatility of this method was demonstrated through a gram-scale experiment and various downstream transformations, highlighting its utility.
- Rhodium(Ⅲ) catalysis,
- Hydrosilylation/cyclization,
- 1, 6-Dienes,
- Silyl enol ether,
- Diastereo- and enantioselectivity
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