Method for producing optically active 2, 3-bisphosphinopyrazine derivative and method for producing optically active phosphine transition metal complex

A method for producing an optically active phosphine transition metal complex represented by the following formula (4), the method comprising:

• a first step of preparing solution A comprising 2,3-dihalogenopyrazine represented by the following formula (1)
• wherein X represents a halogen atom, R1 represents a monovalent substituent, and n is an integer of 0 to 4, and a coordinating solvent which can be coordinated with lithium, and lithiating one of an optically active R-isomer and an optically active S-isomer of a hydrogen-phosphine borane compound represented by the following formula (2)
• wherein R2 and R3 are an optionally substituted linear or branched alkyl group having 1 to 10 carbon atoms, an optionally substituted cycloalkyl group or an optionally substituted phenyl group, R2 and R3 are different from each other, and * represents an asymmetric center on a phosphorus atom, to give a lithiated phosphine borane compound,
• adding solution B comprising the lithiated phosphine borane compound to the solution A to perform an aromatic nucleophilic substitution reaction, and then performing a deboranation reaction by adding a deboranating agent, thereby producing the optically active 2,3-bisphosphinopyrazine derivative represented by the following formula (3) as a result of the deboranation reaction,
• ;
• and
• a second step of reacting the 2,3-bisphosphinopyrazine derivative represented by formula (3) with a transition metal salt of gold, copper or silver to obtain the optically active phosphine transition metal complex represented by the following formula (4),
• M represents a transition metal atom selected from the group consisting of gold, copper and silver;
• and Z− represents an anion.