Method for manufacturing optically active carboxylic acid ester
AssigneeTokyo University of Science Educational Foundation Administrative Organization
InventorsIsamu Shiina, Kenya Nakata, Keisuke Ono
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Abstract
A method that manufacturers an optically active carboxylic acid ester at high yield and high enantioselectivity is provided. An optically active carboxylic acid ester is manufactured at high yield and high enantioselectivity by reacting a racemic carboxylic acid and a specific alcohol or phenol derivatives in a polar solvent having a dipole moment of 3.0 or higher in the presence of an acid anhydride and an asymmetric catalyst, esterifying one enantiomer of the racemic carboxylic acid at high selectivity, and increasing the amount of esterified carboxylic acid by racemizing the optically active carboxylic acid which is the other enantiomer not used in esterification.
Claims19
A method for manufacturing an optically active carboxylic acid ester, the method comprising:
- reacting a racemic carboxylic acid and an alcohol represented by formula (a) below or a phenol derivative represented by formula (b) below under the presence of an acid anhydride and an asymmetric catalyst in a polar solvent with a dipole moment of 3.72 or higher, wherein formula (a) has the structure
- where Ra represents a phenyl group, naphthyl group, anthryl group, or phenanthryl group, which may have a substituent group, and
- formula (b) has the structure
- where Rb represents a phenyl group, naphthyl group, anthryl group, or phenanthryl group, which may have a substituent group, n represents an integer of 1 to 5, and
- in the case that a plurality of Rb is present, they may be the same or different.
Dependencies are inferred from the claim text.