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Diastereoselective formation of β-lactams via a three-component reaction†
Ying Shao,Shijie Tian,Jie Zhu,Shengbiao Tang,Jiangtao Sun
New Journal of Chemistry Pub Date : 05/02/2022 00:00:00 , DOI:10.1039/D2NJ01129H
Abstract

We report herein the synthesis of β-lactams via a three-component reaction of N-hydroxyanilines, diazo compounds and cyclobutenones, which proceeds through a sequential rhodium-catalyzed imine formation and a [2+2] cycloaddition with the in situ generated ketenes from the ring-opening of cyclobutenones. The reaction features broad substrate scope and simplicity of operation, affording densely functionalized β-lactams in moderate to good yields with excellent diastereoselectivity.

Graphical abstract: Diastereoselective formation of β-lactams via a three-component reaction
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