title: Organocatalytic vinylogous Mannich reaction of trimethylsiloxyfuran with isatin-derived benzhydryl-ketimines.
abstract: A family of chiral quaternary 3-aminooxindole butenolides has been synthesized by BINOL-derived phosphoric acid-catalyzed addition of trimethylsiloxyfuran to isatin-derived ketimines. Such a vinylogous Mannich-type reaction was found to produce diastereoisomeric butenolides in good yields and in most cases high enantiomeric excesses. The configurational assignment of the obtained products was safely performed by chemical correlation. A computational study of the transition state allowed rationalizing the obtained stereochemical outcome, highlighting the possible binding modes of the catalyst-imine-nucleophile transition complex.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, Milano, 20133, Italy. Alessandra.silvani@unimi.it.
authors.forename: Giulia
authors.initials: G
authors.lastname: Rainoldi
authors.affiliation: Dipartimento di Chimica, Materiali ed Ing. Chimica 'Giulio Natta', Politecnico di Milano, p.zza Leonardo da Vinci 32, Milano, 20133, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, Milano, 20133, Italy. Alessandra.silvani@unimi.it.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, Milano, 20133, Italy. Alessandra.silvani@unimi.it.
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
mesh_terms: D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D005663:Furans; D007097:Imines; D009570:Nitriles; D010756:Phosphoric Acids; D014297:Trimethylsilyl Compounds; C542835:ketimine; D007510:Isatin; C030242:phosphoric acid