trans-Bis(5-alkoxy- and 5-hydroxy-1-3-η3-cyclohexenyl)palladium Complexes by Palladium(II)-Promoted Addition of Alcohols and Water to 1,2-Dialkyl-1,4-cyclohexadienes

Article abstract of DOI:10.1021/jo00266a022

Aliphatic alcohols and water add to 1,2-dialkyl-1,4-cyclohexadienes in the presence of bis(acetonitrile)palladium dichloride to form trans-bis(5-alkoxy- and 5-hydroxy-1,2-dialkyl-1-3-η³-cyclohexenyl)palladium chloride complexes, respectively.In the alcohol series, the reaction is sensitive to the steric bulk of the alcohol nucleophile.To demonstrate synthetic utility, the derived palladium complexes in the water series were regioselectively and stereoselectively converted by subsequent methoxycarbonylation to the corresponding methyl trans-5-hydroxy-2,3-dialkyl-2-cyclohexene-1-carboxylates.