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Updated: Sep 12, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Diynes via Vinyl Cations
Yan-Xin Zheng1, Li-Gao Liu2, Yu-Yao Zhou1
1State 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.
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.
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