Optically active quarternary ammonium salt with axial chirality, method for producing thereof, and application thereof for asymmetric synthesis of α-amino acid

A method for stereoselectively producing a compound of general formula (XXI):

• wherein
• R5 is alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group;
• allyl or substituted allyl group having 3 to 9 carbon atoms which may be branched or form a cyclic group;
• aralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• heteroaralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• or propargyl or substituted propargyl group which having 3 to 9 carbon atoms which may be branched;
• R6 and R7 are the same or different and are hydrogen atoms, an aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, with proviso excepting that they are hydrogen atoms simultaneously;
• R8 is hydrogen atom;
• aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group;
• aralkyl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• and
• R9 is alkyl group having 1 to 4 carbon atoms;
• comprising;
• alkylating a compound expressed by the general formula (XIX):
• wherein R6 and R7 are the same or different and are hydrogen atoms, an aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, with proviso excepting that they are hydrogen atoms simultaneously;
• R8 is hydrogen atom;
• aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group;
• aralkyl which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• and R9 is alkyl group having 1 to 4 carbon atoms;
• with a compound of general formula (XX):
• R5−W (XX)
• wherein
• R5 is alkyl group having 1 to 6 carbon atoms which may be branched or form a cyclic group;
• allyl or substituted allyl group having 3 to 9 carbon atoms which may be branched or form a cyclic group;
• aralkyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• heteroaralkyl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms, a halogen atom, aryl group which may be substituted with alkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom, or heteroaryl group which may be substituted with alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• or propargyl or substituted propargyl group which having 3 to 9 carbon atoms which may be branched;
• and W is a functional group having leaving ability;
• using the compound of formula (I):
• wherein R1 and R2 are groups independently selected from the group consisting of a hydrogen atom;
• a linear alkyl group having 1 to 6 carbon atoms;
• a branched alkyl group having 2 to 6 carbon atoms;
• a cyclic alkyl group having 3 to 6 carbon atoms;
• a linear alkenyl group having 2 to 6 carbon atoms;
• a branched alkenyl group having 2 to 6 carbon atoms;
• a cyclic alkenyl group having 3 to 6 carbon atoms;
• a linear alkynyl group having 2 to 6 carbon atoms;
• a branched alkynyl group having 3 to 6 carbon atoms;
• a cyclic alkynyl group having 3 to 6 carbon atoms;
• an aralkyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• a heteroaralkyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• an aryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• a heteroaryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, and alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• a (C1 to C3 alkoxy) carbonyl group;
• a carbamoyl group;
• a N-(C1 to C4 alkyl) carbamoyl group;
• and a N,N-di(C1 to C4 alkyl) carbamoyl group (wherein alkyl may be the same or different), and R1 and R2 may be the same or different;
• Ar1 and Ar2 are groups independently selected from the group consisting of an aryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom;
• and a heteroaryl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a halogen atom, and Ar1 and Ar2 may be the same or different;
• X is a halide anion;
• and
• Y and Z are groups independently selected from the group consisting of a hydrogen atom;
• a halogen atom;
• an alkyl group having 1 to 4 carbon atoms;
• and an alkoxy group having 1 to 3 carbon atoms, and Y and Z may be the same or different, or may form a single bond,
• which is pure regarding axial chirality, as a phase-transfer catalyst in a solvent and in the presence of an inorganic base.