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Nickel-Catalyzed Dearomative trans -1,2-Carboamination

2018; American Chemical Society; Volume: 140; Issue: 13 Linguagem: Inglês

10.1021/jacs.8b01726

1943-2984

Lucas W. Hernandez, Ulrich Klöckner, Jola Pospech, Lilian Hauss, David Šarlah,

Asymmetric Synthesis and Catalysis

We describe the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules.