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Updated: Jan 28, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes
You-Yun Zhou1, Christopher Uyeda2
1Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA.
Abstract:
Cycloaddition reactions provide direct and convergent routes to cycloalkanes, making them valuable targets for the development of synthetic methods. Whereas six-membered rings are readily accessible from Diels-Alder reactions, cycloadditions that generate five-membered rings are comparatively limited in scope. Here, we report that dinickel complexes catalyze [4 + 1]-cycloaddition reactions of 1,3-dienes. The C1 partner is a vinylidene equivalent generated from the reductive activation of a 1,1-dichloroalkene in the presence of stoichiometric zinc. Intermolecular and intramolecular variants of the reaction are described, and high levels of asymmetric induction are achieved in the intramolecular cycloadditions using a C 2-symmetric chiral ligand that stabilizes a metal-metal bond.
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