title: Efficient access to enantiopure 1,3-disubstituted isoindolines from selective catalytic fragmentation of an original desymmetrized rigid overbred template.
abstract: An efficient and scalable synthesis of various enantiopure 1,3- disubstituted isoindolines is reported. The base catalyzed nucleophilic fragmentation of a rigid overbred template is established with various substrates to afford the corresponding 1,3-disubstituted isoindoline ester, amide, thioate, 1,3-amino alcohol and isoindolylcarboxylic acid. The crucial rigid overbred template is synthesized in an optically pure form in multigram scale by asymmetric desymmetrization of the corresponding meso compound.
authors.affiliation: Molecular Synthesis Laboratory, Centre of Biomedical Research (CBMR), Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow-226 014, India. gp.pandey@cbmr.res.in.
authors.forename: Ganesh
authors.initials: G
authors.lastname: Pandey
authors.forename: Rajesh
authors.initials: R
authors.lastname: Varkhedkar
authors.forename: Divya
authors.initials: D
authors.lastname: Tiwari
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000577:Amides; D000605:Amino Alcohols; D002264:Carboxylic Acids; D004952:Esters; D054833:Isoindoles; D013438:Sulfhydryl Compounds