title: A cation-directed two-component cascade approach to enantioenriched pyrroloindolines.
abstract: A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.
authors.affiliation: Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. martin.smith@chem.ox.ac.uk.
authors.forename: Jamie R
authors.initials: JR
authors.lastname: Wolstenhulme
authors.forename: Alex
authors.initials: A
authors.lastname: Cavell
authors.forename: Matija
authors.initials: M
authors.lastname: Gredičak
authors.forename: Russell W
authors.initials: RW
authors.lastname: Driver
authors.forename: Martin D
authors.initials: MD
authors.lastname: Smith
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003486:Cyanides; D007211:Indoles; D011758:Pyrroles; C057812:indoline