Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes

Science
You-Yun Zhou, Christopher Uyeda

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 C2-symmetric chiral ligand that stabilizes a metal-metal bond.

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Citations

Jul 17, 2019·ChemMedChem·Guilherme Martins SilvaCarlos Henrique Tomich de Paula da Silva
Jan 31, 2020·Chemical Communications : Chem Comm·Jian Tang, Liang Zhao
May 13, 2020·Chemical Communications : Chem Comm·Arthur R ScheerderDaniël L J Broere
Aug 15, 2020·Science·R Morris BullockYogesh Surendranath
Feb 23, 2019·Science·Keywan Johnson, Daniel Weix
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Dec 15, 2020·Chemical Society Reviews·Wenliang WangJin Xie
Jan 15, 2021·Organic & Biomolecular Chemistry·Beatriz de Pina MarizAna Sofia Pina
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Jan 8, 2022·Journal of the American Chemical Society·Jiao Yu J WangMichelle L Coote

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