Issue 21, 2023

Highly diastereo- and enantioselective synthesis of spiro β-lactams via copper-catalyzed Kinugasa/aldol cascade reaction

Abstract

Spiro β-lactams are important scaffolds in many bioactive compounds and natural products. The development of new synthetic methods for the formation of structurally diversified chiral spiro β-lactams is highly important for the discovery of novel bioactive structures. In this work, a copper(I)-catalyzed asymmetric Kinugasa/aldol-type cascade reaction of ketone-tethered propiolamides and nitrones is developed and a set of novel chiral spiro β-lactams with three contiguous stereogenic centers was achieved in satisfactory yields with high diastereo- and enantioselectivity. Control experiments suggested that a retro-aldol/aldol equilibrium process of the spirobilactam products is critical for the acquisition of high diastereoselectivity.

Graphical abstract: Highly diastereo- and enantioselective synthesis of spiro β-lactams via copper-catalyzed Kinugasa/aldol cascade reaction

Supplementary files

Article information

Article type
Research Article
Submitted
23 Aug. 2023
Accepted
22 Sept. 2023
First published
23 Sept. 2023

Org. Chem. Front., 2023,10, 5383-5388

Highly diastereo- and enantioselective synthesis of spiro β-lactams via copper-catalyzed Kinugasa/aldol cascade reaction

J. Li, H. Ma, X. Zhong, S. Li, J. Zhang, Y. Ao, W. Zhou and Q. Cai, Org. Chem. Front., 2023, 10, 5383 DOI: 10.1039/D3QO01362F

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