Development of Direct Synthesis of Optically Active Compounds

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Several BINAP derivatives have been prepared and their donor-acceptor propeties have been elucidated. New cationic complexes [RuX(binap)(arene)]Y were synthesized in high yields and their catalytic abilities as well as their behaviors in solution have been investigated. Optimization of the reaction conditions of asymmetric hydrogenation of methyl 2-benzamidomethy1-3-oxobutanoate by use of these complexes as catalysts afforded the corresponding alcohol in 98% de and 99% ee. Asymmetric hydrogenation of alpha-alkylidenecyclopentanones, alkylidenelactones, alkenyl ethers, and alpha-keto esters has also been performed in high enantioselectivities. Hydrogenation of various 1,2-benzocycloalkanones and 3-thiacycloalkanones catalyzed by newly developed BINAP-ir(I)-aminophosphine systems afforded the corresponding secondary alcohols in up to 96% ee.