Copper‐Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Diynes via Vinyl Cations
Abstract
Abstract Catalytic asymmetric [2 + 2 + 2] cycloaddition of diynes represents an efficient and atom‐economical strategy for the assembly of valuable chiral cyclic targets in a single step. However, this strategy traditionally relies on the cyclometallation process. Moreover, there are no versatile asymmetric [2 + 2 + 2] cycloaddition methods for diynes that are compatible with C─C double/triple bonds and C─X double bonds. Here, we disclose a copper‐catalyzed asymmetric [2 + 2 + 2] cycloaddition of diynes via vinyl cations. This universal [2 + 2 + 2] cycloaddition is suitable for the asymmetric cycloaddition of diynes with various C─C double/triple bonds and C─X double bonds, leading to a range of valuable chiral hexahydropyrrolocarbazoles, tetrahydropyrrolocarbazoles, and tetrahydropyran[4,3‐b]indoles in generally excellent yields with excellent diastereo‐ and enantioselectivities. Importantly, this protocol features the first asymmetric [2 + 2 + 2] cycloaddition via vinyl cations, and constitutes the first construction of carbon stereocenters in triyne cyclization.
Article Details
Authors (8)
Yan‐Xin Zheng
State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 China
Li‐Gao Liu
Center of Chemistry for Frontier Technologies Department of Chemistry State Key Laboratory of Clean Energy Utilization Zhejiang University Hangzhou 310027 China
Yu‐Yao Zhou
State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 China
Shu‐Ya Yang
State Key Laboratory of Physical Chemistry of Solid Surfaces Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 China
Xin‐Qi Zhu
Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation College of Chemistry and Chemical Engineering Yunnan Normal University Kunming 650500 China
Xin Hong
State Key Laboratory of Advanced Environmental Technology, Department of Environmental Science and Engineering
Bo Zhou
Long‐Wu Ye
State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering Xiamen University Xiamen China