Industrial Synthesis of (+)-cis-Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst [Ru((−)-Me-DuPHOS)(H)(η6-1,3,5-cyclooctatriene)](BF4)

Abstract

Prototypes of new families of precatalysts and catalysts, [Ru((−)-Me-DuPHOS)(H)(η6-1,3,5-cyclooctatriene)](BF4) and the derived “[Ru((−)-Me-DuPHOS)(H)(sol)](BF4)”, are presented. They are used in an industrial, catalytic, enantioselective hydrogenation that leads to (+)-cis-methyl dihydrojasmonate [Eq. (1)]. This stereoisomer is the odorant component of an important, large volume perfumery chemical. P−P=Diphosphane ligand (for example, Me-DuPHOS=1,2-bis((2R,5R)-2,5-dimethylphospholanyl)benzene); sol=solvent.