Citation: Zhirong Yang, Shan Wang, Ming Jiang, Gengchen Li, Long Li, Fangzhi Peng, Zhihui Shao. One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers[J]. Chinese Chemical Letters, ;2024, 35(8): 109518. doi: 10.1016/j.cclet.2024.109518 shu

One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, Kunming 650091, China

lilong@ynu.edu.cn

pengfangzhi@ynu.edu.cn

zhihui_shao@hotmail.com

Received Date: 1 November 2023
Revised Date: 29 December 2023
Accepted Date: 9 January 2024
Available Online: 14 January 2024

Figures(5)

The development of low-cost, earth-abundant and environmentally benign transition metal catalysts, which can catalyze multiple different types of asymmetric reactions, is an important objective in modern asymmetric catalysis. Herein we demonstrate that a chiral Ni/P-Phos catalyst achieves three types of asymmetric reactions: allenylic substitution of racemic allenic ethers, 1,4-hydroalkylation of prochiral 1,3-enynes and double alkylation of newly designed enynyl ether reagents. Three methods complement each other and produce various axially chiral allene derivatives bearing a pyrazolidine-3,5-dione unit, which is widely present in drugs and biologically active molecules with versatile pharmacological activities.
- Nickel,
- Asymmetric catalysis,
- Allenylic substitution,
- Hydroalkylation,
- Double alkylation,
- Allene,
- 1,3-Enyne,
- Pyrazolidine-3,5-dione
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