Efficient Enantio-, Diastereo, E / Z -, and Site-Selective Nickel-Catalyzed Fragment Couplings of Aldehydes, Dienes, and Organoborons.

The enantioselective synthesis of bis-homoallylic alcohols through nickel-catalyzed three-component fragment couplings of simple aldehydes, dienes, and aryl organoborons is disclosed. The reactions proceed through diene dicarbofunctionalization that concurrently forms two C-C bonds and two stereogenic centers. The transformations are promoted by a 5.0 mol % loading of a readily accessible chiral phosphine-nickel complex and afford products with high stereoselectivity.