Patent ID: 8729294

Claim:
A method of producing an optically active 3-substituted-3-formyl-2-hydroxypropanoic acid compound of formula (4): wherein R 1 is (i) a C 1 -C 20 hydrocarbon group optionally having substituent(s) selected from the following Group G1 or (ii) a hydrogen atom, R 2 and R 3 are each independently (i) a C 1 -C 20 hydrocarbon group optionally having substituent(s) selected from the following Group G1, (ii) a C 1 -C 12 alkoxy group optionally having substituent(s) selected from the following Group G1, (iii) a heterocyclic group optionally having substituent(s) selected from the following Group G1 or (iv) a hydrogen atom, and the carbon atom marked with * is an asymmetric carbon atom, which comprises a step of reacting a glyoxylic acid compound of formula (1-1): wherein R 1 is as defined above, and n is an integer of 2 or more, or a glyoxylic acid compound of formula (1-2): wherein R 1 and n are as defined above, with an aldehyde of formula (2): wherein R 2 and R 3 are as defined above, in the presence of an optically active pyrrolidine compound of formula (3): wherein Ar 1 and Ar 2 are each independently (i) a phenyl group optionally having substituent(s) selected from the following Group G2, (ii) a C 1 -C 12 chain hydrocarbon group, (iii) a C 3 -C 12 alicyclic hydrocarbon group or (iv) a hydrogen atom, R 4 is (i) a hydrogen atom, (ii) a fluorine atom, (iii) a hydroxyl group, (iv) a C 1 -C 12 alkoxy group, (v) a C 1 -C 12 fluorinated alkyloxy group or (vi) a silyloxy group reprsented by —OSiR 5 R 6 R 7 , wherein R 5 , R 6 and R 7 are each independently (i) a C 1 -C 8 alkyl group or (ii) a C 6 -C 20 aryl group, and the carbon atom marked with ** is an asymmetric carbon atom; Group G1 is (i) a C 6 -C 20 aryl group optionally having substituent(s) selected from Group G2, (ii) an aromatic heterocyclic group optionally having substituent(s) selected from Group G2, (iii) a C 1 -C 12 alkoxy group, (iv) a C 1 -C 12 alkoxy group having C 6 -C 20 aryl group(s) optionally having substituent(s) selected from Group G2, (v) a halogen atom, or (vi) an oxo group; Group G2 is (i) a C 1 -C 12 alkyl group, (ii) a C 1 -C 12 alkoxy group, (iii) a C 2 -C 13 alkoxycarbonyl group, (iv) a C 1 -C 12 fluorinated alkyl group, (v) a C 2 -C 13 acyl group, (vi) a nitro group, (vii) a cyano group, (viii) a protected amino group, or (ix) a halogen atom.