N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

• Bin Yu,
• Hui Xing,
• De-Quan Yu and
• Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

• stereoselectivity. Products bearing electron-donating groups on the isatin core were obtained with high enantioselectivities. When the R2 group was 1-naphthylmethyl, trityl (Tr) or hydrogen, low ee values were observed. This protocol was successfully applied to the synthesis of 3-aminooxindoles, affording the

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

• Qiao-Wen Jin,
• Zhuo Chai,
• You-Ming Huang,
• Gang Zou and
• Gang Zhao

Beilstein J. Org. Chem. 2016, 12, 725–731, doi:10.3762/bjoc.12.72

• catalysts is reported. The corresponding products containing a tetrasubstituted carbon center attached to a nitrogen atom at the C-3 position of the oxindole were obtained in high yields and with up to 98% ee. Keywords: 3-aminooxindoles; asymmetric catalysis; phosphine catalyst; tetrasubstituted

• stereogenic carbon centers; Introduction Recently, chiral 3-substituted oxindoles have been attractive targets in asymmetric synthesis due to their abundance in the structures of numerous natural products and pharmaceutically active compounds [1]. In particular, the chiral 3-aminooxindoles containing a

Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives

• Giordano Lesma,
• Fiorella Meneghetti,
• Alessandro Sacchetti,
• Mattia Stucchi and
• Alessandra Silvani

Beilstein J. Org. Chem. 2014, 10, 1383–1389, doi:10.3762/bjoc.10.141

• components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were

• methodologies to access chiral 3,3-disubstituted 3-aminooxindoles [16][17][18][19], we looked at isocyanide-based multicomponent reactions as a possible efficient tool to quickly prepare oxindole-based peptidomimetic compounds [20][21][22]. Despite the synthetic efficiency of the Ugi reaction and its wide

• application in combinatorial and medicinal chemistry [23][24][25][26][27][28], to the best of our knowledge a synthesis of 3,3-disubstituted 3-aminooxindoles which relies on isocyanide-based multicomponent reactions has not been unexplored yet. Although in this kind of reaction a new stereogenic center is

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

• Jin-Sheng Yu,
• Feng Zhou,
• Yun-Lin Liu and
• Jian Zhou

Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157

• ][10], 3-aminooxindoles [11][12][13][14][15] and 3-quaternary oxindoles [16][17][18][19][20]. Despite achievements, the catalytic asymmetric synthesis of 3,3-diaryloxindoles has not been reported. This is possibly due to the challenge in the construction of such congested quaternary stereogenic centers

• enantioenriched 3-hydroxyoxindoles [22][23][24]. For the synthesis of chiral 3-aminooxindoles, we developed the first example of catalytic asymmetric addition of nucleophiles to isatin-derived ketoimines using TMSCN [25] and the amination of unprotected 3-prochiral oxindoles using di-tert-butyl azodicarboxylate