Patent ID: 7022869

Claim:
A method of asymmetrically synthesizing an enantiomer of an acylanilide or a derivative thereof comprising: (a) contacting a compound having a ring structure, said compound having the structure of Formula IV: wherein R 1 is alkyl having up to 4 carbons; R 2′ is alkylene having up to 6 carbon atoms; R 9 is hydrogen, or straight, branched or cyclic alkyl; R 10 is straight or branched alkyl, aryl, or R 11 X 3 4 , where R 11 is alkyl and X 4 is alkyl, halogen or aryl; and X 3 is a leaving group; wherein said compound of Formula IV, when opened, provides a substituent having the structure of Formula I: wherein R 1 is alkyl having up to 4 carbons; R 2 is alkyl having up to 6 carbon atoms; and R 3 is CH 2 OR 4 where R 4 is hydrogen or benzyl, C(O)CH 3 , or C(O)OR 5 where R 5 is hydrogen or alkyl; with a compound having a structure of Formula II: R 7 —R 6 —X 1 H Formula II wherein R 6 is a direct link or alkylene having up to 6 carbon atoms; R 7 is alkyl, alkenyl, hydroxyalkyl or cycloalkyl each of up to 6 carbons; or R 7 is phenyl which bears one, two or three substituents independently selected from hydrogen, halogen, nitro, carboxy, carbamoyl and cyano, and alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl, perfluoroalkylsulphonyl, alkoxycarbonyl and N-alkylcarbamoyl each of up to 4 carbon atoms, and phenyl, phenylthio, phenylsulphinyl and phenylsulphonyl; or R 7 is naphthyl; or R 7 is a 5- or 6-membered saturated or unsaturated heterocyclic which contains one, two or three heteroatoms selected from oxygen, nitrogen and sulfur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two halogen, cyano or amino, or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl each of up to 4 carbon atoms, or oxy or hydroxy substituents, or which if sufficiently saturated may bear one or two oxo substituents; and X 1 is oxygen, sulfur, sulphinyl (—SO—), sulphonyl (—SO 2 —), imino (—NH—) or alkylimino (—NR 8 —) where R 8 is alkyl having up to 6 carbon atoms; under conditions sufficient to provide a compound having the structure of Formula III: wherein X 2 is oxygen, sulfur, sulphinyl (—SO—), sulphonyl (—SO 2 —), imino (—NH—), oxidized imino alkylimino (—NR 8 —) where R 8 is alkyl having up to 6 carbon atoms, or oxidized alkylimino; and (b) treating the compound of Formula III under conditions sufficient to provide a pure enantiomer of an acylanilide or a derivative thereof.