Cu-Catalyzed Alkylative Carboxylation of Ynamides with Dialkylzinc Reagents and Carbon Dioxide

Chemistry : a European Journal
Masanori TakimotoZhaomin Hou

Abstract

Alkylative carboxylation of ynamides with CO2 and dialkylzinc reagents using a N-heterocyclic carbene (NHC)-copper catalyst has been developed. A variety of ynamides, both cyclic and acyclic, undergo this transformation under mild conditions to afford the corresponding α,β-unsaturated carboxylic acids, which contain the α,β-dehydroamino acid skeleton. The present alkylative carboxylation formally consists of Cu-catalyzed carbozincation of ynamides with dialkylzinc reagents with the subsequent nucleophilic carboxylation of the resulting alkenylzinc species with CO2 . Dialkylzinc reagents bearing a β-hydrogen atom such as Et2 Zn and Bu2 Zn still afford the alkylated products despite the potential for β-hydride elimination. This protocol would be a desirable method for the synthesis of highly substituted α,β- dehydroamino acid derivatives due to its high regio- and stereoselectivity, simple one-pot procedure, and its use of CO2 as a starting material.

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Citations

Apr 2, 2016·Organic & Biomolecular Chemistry·Sheng WangChanjuan Xi
May 4, 2018·Angewandte Chemie·Andreu TortajadaRuben Martin
Apr 9, 2019·Chemistry, an Asian Journal·Tsuyoshi Mita, Yoshihiro Sato
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Feb 9, 2020·Angewandte Chemie·Shubham DuttaAkhila K Sahoo
Jun 2, 2017·Chemical Communications : Chem Comm·Ryohei DoiYoshihiro Sato
Dec 14, 2016·Topics in Current Chemistry·Xiao-Feng Wu, Feng Zheng
Jul 9, 2021·Chemical Communications : Chem Comm·Manash Protim GogoiAkhila K Sahoo
Sep 19, 2019·The Journal of Organic Chemistry·Luca MassaroPher G Andersson

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