Ruthenium complex, production method of the complex, and production method of optically active secondary alcohols using the complex as catalyst
A ruthenium complex of the following formula (1), a production method thereof, and uses of the ruthenium complex are disclosed. A method for producing the ruthenium complex includes a process of reacting a specific ruthenium complex with a borohydride compound. The ruthenium complex can be used as a catalyst in a production of optically active secondary alcohols.
1 . A ruthenium complex represented by following general formula (1):
wherein a solid line represents a single bond, a double line represents a double bond, a dashed line represents a coordinate bond, and a wavy line represents three-center two-electron bond; B represents a boron atom, N represents a nitrogen atom, and P represents a phosphorus atom; H and H B each represents a hydrogen atom; C, C P1 , C P2 , C a , C N1 , and C N2 each represents a carbon atom; Ru represents a divalent ruthenium ion; R P represents a group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroaryl group, and an aryl group which may have a substituent; R P1 , R P2 , R P3 , and R P4 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, an alkenyl group, an alkoxy group, a halogenoalkoxy group, a hydroxy group, and a halogeno group; R P1 and R P2 may combine with each other to form a ring with C P1 and C P2 , R N1 and R N3 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group; R N2 , R N4 , R N5 , and R N6 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, a halogenoalkyl group, an alkoxy group, and a halogeno group.
2 . The ruthenium complex according to claim 1 , wherein R P is an aryl group which may have a substituent.
3 . The ruthenium complex according to claim 2 , wherein R P3 , R P4 , R N3 , R N4 , R N5 , and R N6 are all hydrogen atoms.
4 . The ruthenium complex according to claim 3 , which is an optically active substance.
5 . A method for producing the ruthenium complex according to claim 1 , comprising a step of reacting a ruthenium complex represented by following general formula (2) with a borohydride compound,
wherein a solid line represents a single bond, a double line represents a double bond, and a dashed line represents a coordinate bond; Cl represents a chlorine atom, H represents a hydrogen atom, N represents a nitrogen atom, and P represents a phosphorus atom; C, C P1 , C P2 , C a , C N1 , and C N2 each represents a carbon atom; Ru represents a divalent ruthenium ion; R P represents a group selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroaryl group, and an aryl group which may have a substituent; R P1 , R P2 , R P3 , and R P4 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, an alkenyl group, an alkoxy group, a halogenoalkoxy group, a hydroxy group, and a halogeno group; R P1 and R P2 may combine with each other to form a ring with C P1 and C P2 ; R N1 and R N3 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group; R N2 , R N4 , R N5 , and R N6 each independently represents a hydrogen atom, or a group selected from the group consisting of an alkyl group, a halogenoalkyl group, an alkoxy group, and a halogeno group.
6 . The method according to claim 5 , wherein the borohydride compound is sodium borohydride.
7 . A method for producing optically active secondary alcohols by catalytic asymmetric hydrogenation of unsymmetrical ketones comprising a step of reacting unsymmetrical ketones in the presence of the ruthenium complex according to claim 4 as a catalyst.