SYNTHESES WITH SULFONES XLVII : STEREOSELECTIVE ACCESS TO 1,3- AND 1,4-DIENES THROUGH HYDROGENOLYSIS OF BENZENESULFONYLDIENES. APPLICATION TO PHEROMONE SYNTHESIS.

Article abstract of DOI:10.1016/S0040-4020(01)90023-7

The stereospecific reduction of EE 2-benzenesulfonyl-1,3-dienes to ZE 1,3-dienes with Grignard reagents under transition metal catalysis is described.Hydrogenolysis of the sulfonyl moiety of 2-benzenesulfonyl-1,4-dienes to ZE 1,4-dienes with sodium dithionite is reported.These techniques have been applied to the stereoselective synthesis of (7E, 9Z) dodecadienyl acetate 3d, (9Z, 11E) tetradecadienyl acetate 3e and (9Z, 12E) tetradecadienyl acetate, 6b.