Binaphthol monophosphoric acid derivative and its use

A binaphthol monophosphate derivative of the following formula (5), (6), (7) or (8):

• wherein each of R1, R2, R3 and R4 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, provided that R1 to R4 are not simultaneously hydrogen, and M is a metal element capable of forning a trivalent metal ion,
• wherein each of R5, R6, R7 and R8 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-20 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-20 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, and M is a metal element capable of forming a trivalent metal ion.

A process for preparing a heterocyclic compound of the following formula (9):

• wherein the symbol * denotes an asymmetric carbon atom, each of R9 and R10 which are independent of each other, is a C2-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkynyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkoxy group, a naphthyl group, a C3-8 cycloalkyl group, a C1-10 alkyl group having a phenyl group, or a C1-10 alkyl group having a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, or R9 may be a hydrogen atom,
• R11 is hydrogen, a C1-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkynyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkoxy group, a naphthyl group, a C3-8 cycloalkyl group, a C1-10 alkyl group having a phenyl group, a C1-10 alkyl group having a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a C1-19 linear or branched alkylcarbonyl group, a C2-19 linear or branched alkenylcarbonyl group, a C2-19 linear or branched alkynylcarbonyl group, a phenylcarbonyl group, a phenylcarbonyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-9 linear or branched alkyl group, a phenylcarbonyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-9 linear or branched alkenyl group, a phenylcarbonyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-9 linear or branched alkynyl group, a naphthylcarbonyl group, a C3-8 cycloalkylcarbonyl group, a C1-9 alkylcarbonyl group having a phenyl group, a C1-9 alkylcarbonyl group having a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-9 linear or branched alkyl group, a C1-19 linear or branched alkyloxycarbonyl group, a phenyloxycarbonyl group, or a phenyloxycarbonyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-9 linear or branched alkyl group,
• provided that R10 and R11 are not the same, and A is an oxygen,
• nitrogen, sulfur or selenium atom;
• which process comprises reacting an aldehyde or a ketone with a diene in the presence of the catalyst for asymmetric synthesis comprising the binaphthol monophosphate derivative of the following formula (5), (6), (7) or (8):
• wherein each of R1, R2, R3 and R4 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, provided that R1 to R4 are not simultaneously hydrogen, and M is a metal element capable of forming a trivalent metal ion,
• wherein each of R5, R6, R7 and R8 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C2-20 linear or branched alkenyl group, a C2-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C2-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, and M is a metal element capable of forming a trivalent metal ion.