Issue 24, 2022

Selective synthesis of functionalized α,β-multi-substituted α-amino cyclopentanones via an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles

Abstract

An efficient approach to construct α-amino cyclopentanones bearing consecutive quaternary and ternary carbon centers is described through an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles. Various α,β-multi-substituted α-amino cyclopentanones can be prepared in good to high yields under mild reaction conditions. This transformation features excellent regio-selectivity, stereospecificity, high step-economy and synthetic diversity, and offers a new protocol to prepare high-value added compounds through Pd-catalyzed addition of boronic acids to nitriles in a selective manner.

Graphical abstract: Selective synthesis of functionalized α,β-multi-substituted α-amino cyclopentanones via an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles

Supplementary files

Article information

Article type
Research Article
Submitted
19 Sep 2022
Accepted
25 Oct 2022
First published
26 Oct 2022

Org. Chem. Front., 2022,9, 6875-6880

Selective synthesis of functionalized α,β-multi-substituted α-amino cyclopentanones via an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles

Q. Ma, C. Li and W. Liao, Org. Chem. Front., 2022, 9, 6875 DOI: 10.1039/D2QO01488B

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