A Convenient Protocol for the Stereocontrolled Synthesis of Olefins with a Homoallylic Type of Functionality

A combination of the Homer–Emmons synthesis of alkyl 2,4-dienoates with their hydrogenation over complex L·Cr(CO)₃ catalysts (L = arene or 3CO) provides a versatile, stereocontrolled approach to olefins with a homoallylic pattern of functional substitution, such as certain insect pheromones or (Z)-prenylated arenes analogous to the “left-side” moiety of bifurcarenone.