Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams

Chenhuan Zhang, Xianqing Wu, Tingting Xia, Jingping Qu and Yifeng Chen ()
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Chenhuan Zhang: East China University of Science and Technology
Xianqing Wu: East China University of Science and Technology
Tingting Xia: East China University of Science and Technology
Jingping Qu: East China University of Science and Technology
Yifeng Chen: East China University of Science and Technology

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Nitrogen-based heterocycles have aroused widespread interest due to their reoccurrence in many pharmaceuticals. Amongst these motifs, the enantioenriched lactams are the ubiquitous scaffolds found in myriad biologically active natural products and drugs. Recently, the transition metal-catalyzed asymmetric carbamoylation has been widely employed as a straightforward arsenal for chiral lactam architecture synthesis, including β-lactam and γ-lactam. However, despite the extensive efforts, there still remains no protocol to accomplish the related δ-lactam synthesis. In this manuscript, the Ni-catalyzed enantioselective carbamoylation of unactivated alkenes by the leverage of reductive dicarbofunctionalization strategy allows for the expedient access to two types of mostly common six-membered lactams: 3,4-dihydroquinolinones and 2-piperidinone in high yield and enantioselectivity. This protocol features with good functional group tolerance, as well as broad substrate scope. The newly developed chiral 8-Quinox skeleton ligand is the key parameter for this transformation, which significantly enhances the reactivity and enantioselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-33425-3

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