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Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

preprint
submitted on 06.11.2018 and posted on 06.11.2018 by Vincent van der Puyl, Joseph Derosa, Keary Engle
We report a regioselective, nickel-catalyzed syn-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with O-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

Funding

NSF-CHE-1800280, NSF-DGE-1346837, NSF-DBI-1359160

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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