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Stereoselective Synthesis of Fully Substituted β-Lactams via Metal–Organo Relay Catalysis

Author:
Chen, Long, Wang, Kai, Shao, Ying, Sun, Jiangtao
Source:
Organic letters 2019 v.21 no.10 pp. 3804-3807
ISSN:
1523-7052
Subject:
beta-lactams, carbon, catalytic activity, chemical reactions, chemical structure, diastereoselectivity, diazo compounds, imines, stereoselective synthesis
Abstract:
A novel three-component reaction of N-hydroxyanilines, enynones, and diazo compounds has been developed via a metal–organo relay catalysis, providing highly functionalized β-lactams containing two quaternary carbon centers in good yields and with excellent diastereoselectivities. This protocol features a sequential reaction of Rh-catalyzed imine formation, Wolff rearrangement, and benzoylquinine-catalyzed Staudinger cyclization using the stable, benign, and readily available N-hydroxyanilines as the N-resources.
Agid:
6445874