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One-pot synthesis of β-lactams by the Ugi and Michael addition cascade reaction

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Abstract

Diversity-oriented synthesis of β-lactams was achieved via Ugi/Michael reaction cascades under mild conditions. The intramolecular hydrogen bonding between the heteroatom from an aldehyde component and the amide NH group controls the chemoselectivity of the Michael reaction versus the aza-Michael reaction. DFT calculation was performed to clarify the mechanism, chemo-selectivity and diastereoselectivity of this work. This one-pot protocol offers a straightforward method to build a diversified β-lactam library for drug discovery.

Graphical abstract: One-pot synthesis of β-lactams by the Ugi and Michael addition cascade reaction

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Publication details

The article was received on 18 May 2018, accepted on 31 Jul 2018 and first published on 02 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01176A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    One-pot synthesis of β-lactams by the Ugi and Michael addition cascade reaction

    X. Gao, C. Shan, Z. Chen, Y. Liu, X. Zhao, A. Zhang, P. Yu, H. Galons, Y. Lan and K. Lu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01176A

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