Abstract: A quaternary ammonium salt represented by formula (5) (wherein R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 10 carbon atoms, R3 represents an alkyl group having 1 to 10 carbon atoms that is optionally substituted with one or more phenyl groups; or a phenyl group that optionally has one or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and a trifluoromethyl group, R4 represents an alkyl group having 1 to 4 carbon atoms, R5 represents an alkyl group having 1 to 10 carbon atoms, C* represents an asymmetric carbon atom, and X? represents a halide ion) can be used as a catalyst having good stability under basic conditions.

Abstract: 1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.

Abstract: Compound (1) or a salt that is useful as an intermediate for the production of a medicine, an agrochemical or the like can be produced by a process including the following steps: (A) reacting an aldehyde (2) with nitromethane to produce a nitroaldehyde; (B) reacting the nitroaldehyde with an alcohol to produce a nitroacetal; (C) reducing the nitroacetal to produce an aminoacetal; (D) protecting an amino group in the aminoacetal to produce a protected aminoacetal; (E) treating the protected aminoacetal with an acid and subsequently with a base and then reacting the resultant product with a cyanating agent to produce a nitrile; (F) hydrolyzing the nitrile to produce a protected amino acid; and (G) substituting a group R5 in the protected amino acid by a hydrogen atom and protecting a carboxyl group therein.

Abstract: An optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester with high optical purity can be obtained by a method of producing an optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester by reacting a 1-amino-2-vinylcyclopropanecarboxylic acid ester with an optically active tartaric acid or an optically active camphorsulfonic acid in a solvent, isolating one diastereomeric salt from the obtained diastereomeric salt mixture and treating the isolated diastereomeric salt with an inorganic acid or a base.

Abstract: A quaternary ammonium salt represented by formula (5) (wherein R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 10 carbon atoms, R3 represents an alkyl group having 1 to 10 carbon atoms that is optionally substituted with one or more phenyl groups; or a phenyl group that optionally has one or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and a trifluoromethyl group, R4 represents an alkyl group having 1 to 4 carbon atoms, R5 represents an alkyl group having 1 to 10 carbon atoms, C* represents an asymmetric carbon atom, and X? represents a halide ion) can be used as a catalyst having good stability under basic conditions.

Abstract: 1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.

Abstract: A process is provided for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): The process includes a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

Abstract: An N-substituted-trans-4-azidopiperidin-3-ol represented by formula (II-1) R1 is as defined below, which is useful as a pharmaceutical intermediate and so on, is produced by reacting an N-substituted-3,4-epoxypiperidine represented by formula (I): wherein R1 represents an aralkyl group having 7 to 24 carbon atoms or an alkyl group having 1 to 12 carbon atoms, with sodium azide in the presence of an inorganic lithium salt.