title: Counterion effects in the catalytic stereoselective synthesis of 2,3'-pyrrolidinyl spirooxindoles.
abstract: A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3'-pyrrolidinyl spirooxindoles with four stereocenters. The addition of NaBArF significantly enhances reactivity, allowing either metal salts or acidic clay to be effective catalysts for the stereoselective reaction.
authors: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA. akfranz@ucdavis.edu.
authors: Jacob P
authors: JP
authors: MacDonald
authors: Benjamin H
authors: BH
authors: Shupe
authors: John D
authors: JD
authors: Schreiber
authors: Annaliese K
authors: AK
authors: Franz
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D011760:Pyrrolidinones / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D058116:Lewis Acids; D000078183:Oxindoles; D011760:Pyrrolidinones; D012821:Silanes; D013141:Spiro Compounds; C507609:crotylsilane; C022960:2-oxindole