title: Organocatalytic direct asymmetric aldol reactions of 3-isothiocyanato oxindoles to ketones: stereocontrolled synthesis of spirooxindoles bearing highly congested contiguous tetrasubstituted stereocenters.
abstract: The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.
authors.affiliation: Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Wen-Bing
authors.initials: WB
authors.lastname: Chen
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Wu
authors.forename: Jing
authors.initials: J
authors.lastname: Hu
authors.forename: Lin-Feng
authors.initials: LF
authors.lastname: Cun
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007211:Indoles; D017879:Isothiocyanates; D007659:Ketones; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; C116609:3-hydroxybutanal