Jacob C Green1, Joseph M Zanghi1, Simon J Meek1. 1. Department of Chemistry , The University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-3290 , United States.
Abstract
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.
A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral n class="Chemical">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 stereodefinedboron-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.
Authors: Ilan Marek; Yury Minko; Morgane Pasco; Tom Mejuch; Noga Gilboa; Helena Chechik; Jaya P Das Journal: J Am Chem Soc Date: 2014-02-10 Impact factor: 15.419