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

Chemical Communications Pub Date: 2017-05-12 DOI: 10.1039/C7CC02426F

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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