Cu(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of Boron/Carbon Vicinal Stereogenic Centers via Insertion Reaction

Abstract

The diastereoselective synthesis of boron and carbon vicinal stereogenic centers is a great challenge in current synthetic chemistry due to the paucity of efficient synthetic strategies. Herein, a Cu-catalyzed diastereo- and enantioselective B–H bond insertion reaction of ene-yne-ketones as furyl-carbene precursors has been developed using chiral bis(oxazolines) (BOX) as the ligand, thus furnishing a series of densely functionalized products (42 examples) bearing both boron and carbon vicinal stereogenic centers in high enantioselectivity and high diastereoselectivity (up to 99% ee and > 20:1 dr) with good yields (up to 98%).

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