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Issue 47, 2017
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Palladium-catalyzed sequential monoarylation/amidation of C(sp3)–H bonds: stereoselective synthesis of α-amino-β-lactams and anti-α,β-diamino acid

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Abstract

Pd-Catalyzed sequential monoarylation/amidation of C(sp3)–H bonds of alanine enabled by a removable 5-methoxyquinolin-8-amine (MQ) auxiliary is described. This process is highly efficient and compatible with a variety of functional groups, providing a general and practical access to various α-amino-β-lactams. The synthetic potential of this protocol is further demonstrated by the stereoselective synthesis of orthogonally protected anti-α,β-diamino acids.

Graphical abstract: Palladium-catalyzed sequential monoarylation/amidation of C(sp3)–H bonds: stereoselective synthesis of α-amino-β-lactams and anti-α,β-diamino acid

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Publication details

The article was received on 29 Mar 2017, accepted on 04 May 2017 and first published on 12 May 2017


Article type: Communication
DOI: 10.1039/C7CC02426F
Citation: Chem. Commun., 2017,53, 6351-6354
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    Palladium-catalyzed sequential monoarylation/amidation of C(sp3)–H bonds: stereoselective synthesis of α-amino-β-lactams and anti-α,β-diamino acid

    P. Ling, S. Fang, X. Yin, Q. Zhang, K. Chen and B. Shi, Chem. Commun., 2017, 53, 6351
    DOI: 10.1039/C7CC02426F

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