biostudies-literature00480Green JCUniversity of North Carolina at Chapel HillNational Institute of General Medical SciencesNIGMS NIH HHS1704-1709https://www.ebi.ac.uk/biostudies/studies/S-EPMC7180160biostudies-literatureUnknown142(4)A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable γ,γ-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.Journal of the American Chemical SocietyDiastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.PMC7180160R01 GM116987R01GM116987Meek SJGreen JCZanghi JM48falseDiastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable γ,γ-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.2020-01-01T00:00:00Z2020 Jan2024-11-14T13:44:12.379Z2021-02-21T03:43:07ZS-EPMC71801603193476610.1021/jacs.9b11529