Diastereoselective formation of β-lactams via a three-component reaction. (18th May 2022)

• Record Type: Journal Article
• Authors: Shao, Ying; Tian, Shijie; Zhu, Jie; Tang, Shengbiao; Sun, Jiangtao
• Is Part Of: New journal of chemistry. Volume 46:Number 21(2022)
• Page Start: 9989
• Page End: 9993
• Publication Date: 2022-05-18
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj01129h
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A highly diastereoselective three-component reaction of N -hydroxyanilines, diazo compounds and cyclobutenones to form densely functionalized β-lactams has been realized. 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.