title: Dual behavior of isatin-based cyclic ketimines with dicarbomethoxy carbene: expedient synthesis of highly functionalized spirooxindolyl oxazolidines and pyrrolines.
abstract: A highly stereo-, regio-, and chemoselective method has been devised for the synthesis of a wide range of spirooxindolyl oxazolidines via an intermolecular 1,3-dipolar cycloaddition of carbonyl ylides generated from dimethyl diazomalonate and aromatic aldehydes, with cyclic ketimines using 5 mol % of Rh2(OAc)4 under mild conditions. Similarly, highly functionalized spirooxindolyl pyrrolines have also been prepared through 1,3-dipolar cycloaddition of azomethine ylides generated from dimethyl diazomalonate and cyclic ketimines, with dimethyl acetylenedicarboxylate.
authors.affiliation: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500 007, India.
authors.forename: T
authors.initials: T
authors.lastname: Rajasekaran
authors.forename: G
authors.initials: G
authors.lastname: Karthik
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
mesh_terms: D001391:Azo Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D007097:Imines; D007211:Indoles; D009570:Nitriles; D010080:Oxazoles; D011758:Pyrroles; D013141:Spiro Compounds; D013882:Thiosemicarbazones; C512188:azomethine; C542835:ketimine; C064210:oxazolidine; C013231:pyrroline; D007510:Isatin