Periselective and enantioselective carbonyl-ene reaction of isoprene with fluoroalkyl glyoxylate catalysed by modified binaphthol-titanium complex: Asymmetric catalytic synthesis of enantiomerically pure ipsdienol

The asymmetric reaction of trifluoroethyl glyoxylate 3d with isoprene 4 catalysed by the modified binaphthol-titanium complex 2b provides the ene product 5d in high periselectivity (92%) and complete enantioselectivity, which can be converted to ipsdienol 1, a component of the aggregation pheromone of the bark beetle, genus lps, in enantiomerically pure form.