Allenamides Get Greener with CO2

  • ChemPubSoc Europe Logo
  • Author: Pamela Alsabeh
  • Published Date: 23 May 2016
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Allenamides Get Greener with CO<sub>2</sub>

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Allenamides are an important synthetic building block in organic chemistry. Producing nitrogen-containing heterocycles from these precursors is of particular interest among the synthetic community. Reacting allenamides with a C1 source such as CO2 allows the synthesis of valuable amino acid derivatives.


Masanori Takimoto, Zhaomin Hou, and colleagues, RIKEN, Saitama, Japan, have developed an N-heterocyclic carbene-copper complex which catalyzes the alkylative carboxylation of allenamides with CO2 and dialkylzinc reagents. Using CO2 at a pressure of 1 atm, 1.5 equiv. of dialkylzinc reagent and 5 mol% of copper catalyst, a broad scope of (Z)-α,β-dehydro-β-amino acid esters (pictured) was accessible in good yields.


The reaction has excellent regio- and stereoselectivity, with the alkyl group introduced at the less hindered allenamide γ-carbon atom, and the carboxyl group at the β-carbon. The carboxylation proceeds at room temperature and tolerates a variety of substrates, including both cyclic and acyclic compounds. The method could contribute to the implementation of greener technologies using allenamides and CO2.


 

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