121974-35-4Relevant articles and documents
Palladium-catalyzed asymmetric allylic alkylation of 3-amino-2-oxindoles: Synthesis of 3-allyl-3-amino-2-oxindoles
Jayakumar, Samydurai,Kesavan, Venkitasamy,Kumarswamyreddy, Nandarapu
, (2021/09/13)
Tartrate derived bi(oxazoline) ligand with palladium (II) species catalyzed asymmetric allylic alkylation reaction to access highly valuable 3-allyl-3-amino-2-oxindoles with vicinal quaternary and tertiary stereocenters in very good yields (up to 91%) and excellent enantioselectivity (up to 98% ee) with moderate to good diastereoselectivity (up to 5:1). The synthetic utility of 3-allyl-3-amino-2-oxindole was further demonstrated to construct spiro(oxindole-3,2′-pyrrolidine) with consecutive one quaternary and three tertiary chiral centers in good stereoselectivity (dr = 8:1 and 80% ee) through metal-free intramolecular iodocyclization reaction.
Organocatalytic direct asymmetric aldol reactions of 3-isothiocyanato oxindoles to ketones: Stereocontrolled synthesis of spirooxindoles bearing highly congested contiguous tetrasubstituted stereocenters
Chen, Wen-Bing,Wu, Zhi-Jun,Hu, Jing,Cun, Lin-Feng,Zhang, Xiao-Mei,Yuan, Wei-Cheng
supporting information; experimental part, p. 2472 - 2475 (2011/07/07)
Chemical equations presented. 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.