Method for producing optically active substance, optically active substance, method for producing chiral molecule, and chiral molecule

A method for producing a chiral molecule, the method comprising an asymmetric stabilization, wherein a reagent is allowed to act on an optically active substance of a first chiral molecule having a half-life of enantiomeric excess of shorter than 10 hours at 50° C., of which one enantiomer is present in excess over the other enantiomer, thereby converting the optically active substance of the first chiral molecule to an optically active substance of a second chiral molecule having a longer half-life of enantiomeric excess, wherein:

• the first chiral molecule is represented by any of General Formulas (2) to (3), (4a), (4b), (7) and (8) below:
• in General Formula (2), R21 and R22 each independently represent a hydrogen atom or a substituent;
• R23 to R26 each independently represent a hydrogen atom or a substituent;
• X21 represents O, S, or NR27, where R27 represents a substituent;
• and n2 represents an integer from 1 to 10;
• in General Formula (3), R31 and R32 each independently represent a substituent, and R33 to R37 each independently represent a hydrogen atom or a substituent;
• in General Formula (4a), R41 to R43 each independently represent a substituent;
• n4 represents an integer from 1 to 10;
• and a benzene ring is fused in place of any —CH2CH2— constituting the cycloalkylene ring of General Formula (4a) or no benzene ring is fused to the cycloalkene ring;
• in General Formula (4b), R44 to R48 each independently represent a substituent;
• in General Formula (7), R71 and R72 each independently represent a hydrogen atom or a substituent;
• in General Formula (8), R81 and R82 each independently represent a hydrogen atom or a substituent;
• and R83 represents a substituent,
• all of said substituents are independently selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, an alkylthio group having from 1 to 20 carbon atoms, an alkyl-substituted amino group having from 1 to 20 carbon atoms, an acyl group having from 2 to 20 carbon atoms, an aryl group having from 6 to 40 carbon atoms, a heteroaryl group having from 3 to 40 carbon atoms, a diarylamino group having from 12 to 40 carbon atoms, a substituted or unsubstituted carbazolyl group having from 12 to 40 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an alkynyl group having from 2 to 10 carbon atoms, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a haloalkyl group having from 1 to 10 carbon atoms, an amide group, an alkylamide group having from 2 to 10 carbon atoms, a trialkylsilyl group having from 3 to 20 carbon atoms, a trialkylsilylalkyl group having from 4 to 20 carbon atoms, a trialkylsilylalkenyl group having from 5 to 20 carbon atoms, a trialkylsilylalkynyl group having from 5 to 20 carbon atoms, and a nitro group;
• and
• the reagent is an epoxidizing agent, an alkyllithium reagent, an alkylmagnesium reagent, or a metal alkoxide reagent.

A method for producing a chiral molecule, the method comprising:

• an asymmetric stabilization, wherein a reagent is allowed to act on an optically active substance of a first chiral molecule having a half-life of enantiomeric excess of shorter than 10 hours at 50° C., of which one enantiomer is present in excess over the other enantiomer, thereby converting the optically active substance of the first chiral molecule to an optically active substance of a second chiral molecule having a longer half-life of enantiomeric excess,
• allowing an asymmetry inducer to act on a chiral molecule having a half-life of enantiomeric excess of shorter than 10 hours at 50° C. before the asymmetric stabilization, thereby increasing abundance of one enantiomer of the chiral molecule to obtain the first chiral molecule, of which one enantiomer of the chiral molecule is present in excess over the other enantiomer of the chiral molecule, wherein
• the chiral molecule and the first chiral molecule are represented by any of General Formulas (1) to (3), (4a), (4b), (7) and (8) below:
• in General Formula (1), R11 to R14 each independently represent a hydrogen atom or a substituent;
• X11 represents O, S, or NR15, where R15 represents a substituent;
• and n1 represents an integer from 1 to 10;
• in General Formula (2), R21 and R22 each independently represent a hydrogen atom or a substituent;
• R23 to R26 each independently represent a hydrogen atom or a substituent;
• X21 represents O, S, or NR27, where R27 represents a substituent;
• and n2 represents an integer from 1 to 10;
• in General Formula (3), R31 and R32 each independently represent a substituent, and R33 to R37 each independently represent a hydrogen atom or a substituent;
• in General Formula (4a), R41 to R43 each independently represent a substituent;
• n4 represents an integer from 1 to 10;
• and a benzene ring is fused in place of any —CH2CH2— constituting the cycloalkylene ring of General Formula (4a) or no benzene ring is fused to the cycloalkene ring;
• in General Formula (4b), R44 to R48 each independently represent a substituent;
• in General Formula (7), R71 and R72 each independently represent a hydrogen atom or a substituent;
• in General Formula (8), R81 and R82 each independently represent a hydrogen atom or a substituent;
• and R83 represents a substituent,
• all of said substituents are independently selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, an alkylthio group having from 1 to 20 carbon atoms, an alkyl-substituted amino group having from 1 to 20 carbon atoms, an acyl group having from 2 to 20 carbon atoms, an aryl group having from 6 to 40 carbon atoms, a heteroaryl group having from 3 to 40 carbon atoms, a diarylamino group having from 12 to 40 carbon atoms, a substituted or unsubstituted carbazolyl group having from 12 to 40 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an alkynyl group having from 2 to 10 carbon atoms, an alkoxycarbonyl group having from 2 to 10 carbon atoms, an alkylsulfonyl group having from 1 to 10 carbon atoms, a haloalkyl group having from 1 to 10 carbon atoms, an amide group, an alkylamide group having from 2 to 10 carbon atoms, a trialkylsilyl group having from 3 to 20 carbon atoms, a trialkylsilylalkyl group having from 4 to 20 carbon atoms, a trialkylsilylalkenyl group having from 5 to 20 carbon atoms, a trialkylsilylalkynyl group having from 5 to 20 carbon atoms, and a nitro group;
• the reagent is an epoxidizing agent, an alkyllithium reagent, an alkylmagnesium reagent, or a metal alkoxide reagent;
• and
• the asymmetry inducer is a sugar chain derivative including a structure in which a phenyl group is linked to a cellulose or an amylose via an ester group or a urethane group.