Catalytic Reductive Carbon-Carbon Bond-Forming Reactions of Alkynes

Tetrahedron 14(22),3619-3625, DOI: 10.1016/j.tetasy.2003.07.010

Enantioselective nickel/phosphine-catalyzed reductive coupling of alkynes and aldehydes provides rapid access to synthetically useful allylic alcohols with high enantiomeric excess. A related reaction involving epoxides is enantiospecific, transforming alkynes and chiral terminal epoxides into enantiomerically pure homoallylic alcohols containing a trisubstituted olefin of defined geometry. A gram-scale example of each of these processes is described."