Method for producing optically active amines

A method for producing a chiral amine represented by the formula [VII]:

• (wherein R4 and R5 independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an optionally substituted heteroaryl group or an optionally substituted cycloalkyl group, or
• R4 and R5 together with the adjacent nitrogen atom may form a ring by binding to each other at the ends thereof;
• R6, which is different from R7, represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an optionally substituted cycloalkyl group or an optionally substituted heteroaryl group, and
• R7 represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an optionally substituted heteroaryl group, an optionally substituted cycloalkyl group, a carboxyl group, an esterified carboxyl group, a cyano group or an amide group, or
• R6 and R7 together with the adjacent carbon atom may form a ring by binding to each other at the ends thereof;
• and
• the symbol “*” represents a chiral carbon atom), comprising reacting an amine represented by the formula [III]:
• (wherein R4 and R5 have the same meanings as defined above)
• and a ketone represented by the formula [IV]:
• (wherein R6 and R7 have the same meanings as defined above)
• with a metal compound represented by the formula [V]:
• MXn [V]
• (wherein M represents an atom selected from the group consisting of boron, aluminum, zinc, titanium and zirconium, n represents the valence number of M, and X represents an alkoxy group, an aryloxy group, an acyloxy group, a sulfoxy group, a trifluoromethanesulfoxy group or halogen)
• to produce a metal-containing aminoalcohol compound represented by the formula [VI]:
• (wherein R4, R5, R6, R7, M, n and X have the same meanings as defined above), and then subjecting the metal-containing aminoalcohol compound to asymmetric transfer hydrogenation in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand.

A method for producing tamuslosin represented by the formula [II-a]:

• (wherein Me represents a methyl group, Et represents an ethyl group, and the symbol “*” represents a chiral carbon atom), or an acid addition salt thereof, comprising subjecting an imine compound represented by the formula [I-a]:
• (wherein Me and Et have the same meanings as defined above)
• to asymmetric transfer hydrogenation in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand, and
• if desired, converting the resulting product into an acid addition salt thereof.