title: Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter.
abstract: Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and  moderate to good enantioselectivity. Diastereoselectivity was also investigated in the construction of contiguous tertiary and quaternary stereocenters. The use of acrolein as Michael acceptor led to an interesting tricyclic derivative, a pyrroloisoindolinone analogue, via a tandem conjugated addition/cyclization reaction.
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy. scorzelli.francesco@tiscali.it.
authors.forename: Francesco
authors.initials: F
authors.lastname: Scorzelli
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy. toniadimola@libero.it.
authors.forename: Antonia
authors.initials: A
authors.lastname: Di Mola
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy. lpalombi@unisa.it.
authors.forename: Laura
authors.initials: L
authors.lastname: Palombi
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084-Fisciano, SA, Italy. amassa@unisa.it.
authors.forename: Antonio
authors.initials: A
authors.lastname: Massa
mesh_terms: D000171:Acrolein / Q000737:chemistry; D064751:Ammonium Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D003500:Cyclization; D054833:Isoindoles / Q000737:chemistry*; D015394:Molecular Structure; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D064751:Ammonium Compounds; D002930:Cinchona Alkaloids; D054833:Isoindoles; D010797:Phthalimides; C037432:phthalimidine; D002244:Carbon; D000171:Acrolein
keywords: asymmetric catalysis; chiral phase transfer catalysts; conjugate addition; nitrogen heterocycles; synthetic methods