Enantioselective and regioselective nickel-catalyzed multicomponent coupling of chiral allenes, aromatic aldehydes, and silanes

A detailed account of the development of a recently developed, nickel-catalyzed multicomponent coupling of chiral allenes, aromatic aldehydes, and silanes is described. The axial chirality of the allene is transferred completely to the product, a trisubstituted Z-allylic alcohol protected as a silyl ether. A very high preference for sp rather than sp2 coupling is observed, and differentially substituted allenes undergo highly site-selective coupling. These transformations represent the first enantioselective multi-component coupling processes of allenes.