Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones

Organic & Biomolecular Chemistry
Lei WangYudao Ma

Abstract

An enantioselective conjugate addition of boron to α,β-unsaturated ketones catalysed by either a N-heterocyclic carbene or a copper-carbene complex generated in situ from a new chiral bicyclic triazolium based on [2.2]paracyclophane is presented. The dual chiral carbene-copper catalyst has significant advantages over its carbene counterpart as an organocatalyst in asymmetric β-boration of acyclic enones, giving a variety of chiral β-boryl ketones in good yields and enantioselectivities. This is a successful example of employing the same N-heterocyclic carbene in one catalytic reaction as both an organocatalyst and a ligand for transition metal catalysis.

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Citations

Jul 20, 2016·Chemical Reviews·Emily C NeeveTodd B Marder
Dec 13, 2016·Chemical Society Reviews·Ana B CuencaElena Fernández
Mar 29, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Qingxia YaoWenzeng Duan
Jun 14, 2016·Chemistry : a European Journal·Roman SavkaHerbert Plenio
Jan 2, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yanmei WenXinhuang Kang
Nov 5, 2020·Organic & Biomolecular Chemistry·Kanak Kanti DasSantanu Panda
Jul 2, 2021·Angewandte Chemie·Gaurav DahiyaAaron Aponick
Sep 30, 2021·Chemical Society Reviews·Wenbo MingTodd B Marder
Nov 18, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Daven FosterReto Dorta

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