A Stereoselective Synthesis of Tri-substituted Alkenes. The Nickel-Catalysed Coupling of Grignard Reagents with 6-Alkyl-3,4-dihydro-2H-pyrans.

Article abstract of DOI:10.1016/S0040-4039(00)86058-X

The nickel-catalysed coupling of certain Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans is highly stereoselective and gives tri-substituted alkenes with retention of configuration.The method was applied to the synthesis of (E)-3-Acetoxy-7-methyl-6-nonene, the aggregation pheromone of the square-necked grain beetle.