Enantioselective desymmetrization of meso-cyclic anhydrides catalyzed by hexahydro-1H-pyrrolo[1,2-c] imidazolones

• Published in: Tetrahedron letters Vol. 42; no. 3; pp. 411 - 414
• Main Authors: Uozumi, Y, Yasoshima, K, Miyachi, T, Nagai, S
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 15.01.2001
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; nucleophilic catalyst; ISOPROPYL HEMIESTERS; SECONDARY ALCOHOLS; enantioselective desymmetrization; ASYMMETRIC-SYNTHESIS; pyrrolo[1,2-c]imidazolone; HETEROCYCLES; ACYLATION; ESTERIFICATION; DMAP; ACID ANHYDRIDES; NONENZYMATIC KINETIC RESOLUTION

Asymmetric methanolysis of meso cyclic carboxylic anhydrides including hexahydrophthalic anhydride proceeded in toluene in the presence of (6R,7aS)-(2-aryl-6-hydroxy)hexahydro- 1H-pyrrolo[1,2-c]imidazol-1-one to give the corresponding desymmetrized mono ester acids (e.g. (1S,2R)-2- (methoxycarbonyl)...