Citation: Junwei Wang, Lei Zhao, Chen Zhu, Ben Ma, Xiaolong Xie, Jian Liu, Shiyun He, Magnus Rueping, Kun Zhao, Lihong Hu. Transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates: Access to different sized medium-sized heterocycles[J]. Chinese Chemical Letters, ;2022, 33(10): 4549-4558. doi: 10.1016/j.cclet.2022.01.063 shu

Transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates: Access to different sized medium-sized heterocycles

Junwei Wang ^{a, 1} ,
Lei Zhao ^{a, 1} ,
Chen Zhu ^{b, 1} ,
Ben Ma ^a ,
Xiaolong Xie ^a ,
Jian Liu ^a ,
Shiyun He ^a ,
Magnus Rueping ^{b, *,} ,
Kun Zhao ^{c, *,} ,
Lihong Hu ^{a, *,}

a.
Jiangsu Key Laboratory for Functional Substances of Chinese Medicine, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
b.
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia
c.
Department of Medicinal Chemistry, Key Laboratory of Chemical Biology, School of Pharmacy, Cheeloo College of Medicine, Shandong University, Ji'nan 250012, China

magnus.rueping@kaust.edu.sa

kzhao2013@sdu.edu.cn

lhhu@njucm.edu.cn

Received Date: 8 November 2021
Revised Date: 19 January 2022
Accepted Date: 23 January 2022
Available Online: 31 January 2022

Figures(9)

Divergent synthesis of medium-sized rings with controllable ring sizes represents a longstanding challenge in organic synthesis. Herein, we developed a transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates by controlling the steric hindrance of substituent. Different from reported alkoxide-triggered annulations, this process undergoes a regiodivergent allylation of para-quinone methides followed by 1, 6-addition reaction, providing a new route to selectively synthesize seven- to ten-membered nitrogen-containing heterocycles in high yields with excellent regioselectivities. This protocol features a broad substrate scope, wide functional group tolerance as well as operational simplicity. The reaction mechanism was investigated by conducting a series of control experiments as well as DFT calculations and the origins of the regioselectivities of the cycloaddition process were rationalized.
- Medium-sized rings,
- Divergent cycloaddition,
- Regioselectivity,
- para-Quinone methides,
- Vinylethylene carbonates
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