Issue 13, 2019

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

Abstract

Transition-metal-free visible-light photoredox catalyzed decarboxylative radical addition has been developed for the construction of α,β-diamino esters from amino acids with glyoxylic oxime ethers under mild conditions. Cyclic and chain amino acids, dipeptides, and simple aliphatic acids are amenable to this addition as the alkyl radical source. A variety of α,β-diamino esters with broad functional groups were synthesized in satisfactory yields at room temperature. The employment of acridinium as the photocatalyst and its potential scalability also demonstrate the synthetic value in practice.

Graphical abstract: Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

Supplementary files

Article information

Article type
Research Article
Submitted
21 mrt 2019
Accepted
29 apr 2019
First published
01 mei 2019

Org. Chem. Front., 2019,6, 2245-2249

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

G. Wu, J. Wang, C. Liu, M. Sun, L. Zhang, Y. Ma, R. Cheng and J. Ye, Org. Chem. Front., 2019, 6, 2245 DOI: 10.1039/C9QO00407F

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