title: N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles.
abstract: A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Xu
authors.forename: Chengli
authors.initials: C
authors.lastname: Mou
authors.forename: Tingshun
authors.initials: T
authors.lastname: Zhu
authors.forename: Bao-An
authors.initials: BA
authors.lastname: Song
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001573:Benzoin / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D007097:Imines; D007211:Indoles; D009570:Nitriles; C542835:ketimine; C030011:carbene; D007510:Isatin; D001573:Benzoin; D008697:Methane