Process for production of optically active compounds
View Patent ↗The present invention provides a method for producing an optically active β-hydroxy ester compound represented by the general formula: wherein R 1 represents an optionally substituted hydrocarbon group and the like, R 2 represents a nitrogen-containing heterocyclic group different from R 1 , which is represented by the general formula: wherein the ring may be substituted and the like, R 3 represents an optionally substituted hydrocarbon group and the like, R 4 and R 5 represent, the same or different, a hydrogen atom, a halogen atom and the like, the symbol “*” represents an optically active center, which comprises reacting in the presence of a cinchona alkaloid and the like a compound represented by the general formula: wherein R 1 and R 2 are as defined above with a compound represented by the general formula: wherein R 3 , R 4 and R 5 are as defined above, and X is a halogen atom.
1. A method for producing an optically active β-hydroxy ester compound represented by the general formula:
wherein
R 1 represents an optionally substituted aromatic hydrocarbon group,
R 2 represents a 5- or 6-membered nitrogen-containing heterocyclic group which is represented by the general formula:
wherein the ring may be substituted, and may have one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in addition to the nitrogen atom in the formula, and may have one or more double bonds in addition to the double bond in the formula; or the general formula:
wherein the ring may be substituted, and may have one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in addition to the nitrogen atom in the formula, and may have one or more double bonds in addition to the double bond in the formula, provided that R 2 is not a group represented by the general formula:
wherein L represents a protecting group,
R 3 represents an optionally substituted hydrocarbon group,
R 4 and R 5 are the same or different, and represent a hydrogen atom, or an optionally substituted hydrocarbon group, or R 4 and R 5 may be taken together to form a ring, wherein said ring may be substituted,
the symbol “*” represents an optically active center, or a salt thereof, which comprises reacting, in the presence of a cinchona alkaloid selected from the group consisting of cinchonine, cinchonidine, quinine and quinidine or a salt thereof, a compound represented by the general formula:
wherein R 1 and R 2 are as defined above or a salt thereof with a compound represented by the general formula:
wherein R 3 , R 4 and R 5 are as defined above, and X is a halogen atom, or a polymer thereof or a salt thereof.
2. The method according to claim 1 , which further comprises adding a base.
3. The method according to claim 2 , wherein the base is pyridine.
4. The method according to claim 1 , wherein R 2 is an optionally substituted 2-pyridyl group or 4-imidazolyl group.