Issue 53, 2023

Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones

Abstract

Using newly designed α-imino amide surrogates and azlactones as amphiphilic reactants, catalyzed by a chiral bifunctional guanidine, the construction of chiral 3,4-diaminopyrrolidine-2,5-diones and their derivatives was realized via formal [3+2]-cyclization. The role of guanidine as a multiple hydrogen bond donor was demonstrated by DFT calculations.

Graphical abstract: Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones

Supplementary files

Article information

Article type
Communication
Submitted
10 Mar 2023
Accepted
05 Jun 2023
First published
08 Jun 2023

Chem. Commun., 2023,59, 8250-8253

Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones

P. Ruan, C. Zhang, J. Wu, F. Xiao, Y. Zhang, Q. Tan, Z. Su, X. Feng and X. Liu, Chem. Commun., 2023, 59, 8250 DOI: 10.1039/D3CC01203D

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