Citation: Ji-Jia Zhou, Li-Gao Liu, Zhen-Tao Zhang, Hao-Xuan Dong, Xin Lu, Zhou Xu, Xin-Qi Zhu, Bo Zhou, Long-Wu Ye. Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement[J]. Chinese Chemical Letters, ;2025, 36(9): 110870. doi: 10.1016/j.cclet.2025.110870 shu

Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement

Ji-Jia Zhou ^{a, 1} ,
Li-Gao Liu ^{a, 1} ,
Zhen-Tao Zhang ^{a, 1} ,
Hao-Xuan Dong ^a ,
Xin Lu ^{a, *,} ,
Zhou Xu ^{b, *,} ,
Xin-Qi Zhu ^c ,
Bo Zhou ^a ,
Long-Wu Ye ^{a, c, d, *,}

a.
State Key Laboratory of Physical Chemistry of Solid Surfaces and Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
b.
Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, Xuzhou 221004, China
c.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China
d.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

xinlu@xmu.edu.cn

xuzhou@xzhmu.edu.cn

longwuye@xmu.edu.cn

Received Date: 22 October 2024
Revised Date: 5 January 2025
Accepted Date: 16 January 2025
Available Online: 23 January 2025

Figures(8)

The Meinwald rearrangement has proven to be one of the most useful tools in organic synthesis. However, examples of asymmetric Meinwald rearrangements are quite scarce, and these reactions have so far been limited to the use of chiral Brønsted acids as catalysts. Here, we report a copper-catalyzed asymmetric cascade cyclization/Meinwald rearrangement reaction, allowing the practical and atom-economic synthesis of a range of chiral tricyclic pyrroles bearing a chiral oxa-quaternary carbon stereocenter in high yields and enantioselectivities. Thus, this protocol not only represents the first transition-metal-catalyzed enantioselective Meinwald rearrangement, but also constitutes the first example of asymmetric formal monocarbon insertion into C–O bond of ester. Moreover, theoretical calculations provide further evidence for this multiple cascade cyclization and elucidate the origin of enantioselectivity.
- Meinwald rearrangement,
- Diyne cyclization,
- Asymmetric catalysis
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