title: Enantioselective aldol reaction between isatins and cyclohexanone catalyzed by amino acid sulphonamides.
abstract: Sulphonamides derived from primary α-amino acid were successfully applied to catalyze the aldol reaction between isatin and cyclohexanone under neat conditions. More interestingly, molecular sieves, as privileged additives, were found to play a vital role in achieving high enantioselectivity. Consequently, high yields (up to 99%) along with good enantioselectivities (up to 92% ee) and diastereoselectivities (up to 95:5 dr) were obtained. In addition, this reaction was also conveniently scaled up, demonstrating the applicability of this protocol.
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University, Changsha, P.R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
authors.forename: Qi
authors.initials: Q
authors.lastname: Liu
authors.forename: Qing
authors.initials: Q
authors.lastname: Hao
authors.forename: Yanhua
authors.initials: Y
authors.lastname: Sun
authors.forename: Yiming
authors.initials: Y
authors.lastname: Luo
authors.forename: Hua
authors.initials: H
authors.lastname: Yang
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D003512:Cyclohexanones; D013449:Sulfonamides; C036468:cyclohexanone; D007510:Isatin
keywords: 3-cycloalkanone-3-hydroxy-2-oxindole; asymmetric synthesis; molecular sieves; neat conditions; organocatalysis