title: Tertiary amine-catalyzed chemoselective and asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones.
abstract: A chemo- and enantioselective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones was catalyzed by a β-ICD O-MOM ether 1c, affording spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif in outstanding ee values (up to >99%). More electrophiles, such as N-phenylmaleimide, have been also utilized to deliver complex spirocyclic 2-oxindoles with good results.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Peng
authors.forename: Xin
authors.initials: X
authors.lastname: Huang
authors.forename: Lin
authors.initials: L
authors.lastname: Jiang
authors.forename: Hai-Lei
authors.initials: HL
authors.lastname: Cui
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000588:Amines; D002254:Carbonates; C116442:propargylic sulfone; D007510:Isatin