Issue 23, 2023

Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

Abstract

A palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates with methylene cyclic carbamates has been successfully developed. An array of enantioenriched products bearing nitrile-containing acyclic quaternary carbon stereocenters were obtained in high yields with good enantioselectivities (up to 99% yield and 93% ee). This method provides a new tactic for the construction of chiral nitrile-containing acyclic quaternary carbon stereocenters.

Graphical abstract: Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

Supplementary files

Article information

Article type
Research Article
Submitted
30 Sep 2023
Accepted
20 Oct 2023
First published
20 Oct 2023

Org. Chem. Front., 2023,10, 5971-5977

Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

Q. Bao, T. Sun, Y. Zhang, Z. Wang, Y. You, Z. Ge, M. Zhou, J. Zhao and W. Yuan, Org. Chem. Front., 2023, 10, 5971 DOI: 10.1039/D3QO01605F

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