1290607-19-0Relevant articles and documents
Amino-indanol-catalyzed asymmetric michael additions of oxindoles to protected 2-amino-1-nitroethenes for the synthesis of 3,3′-disubstituted oxindoles bearing α,β-diamino functionality
Liu, Xiong-Li,Wu, Zhi-Jun,Du, Xi-Lin,Zhang, Xiao-Mei,Yuan, Wei-Cheng
, p. 4008 - 4017 (2011)
An organocatalytic asymmetric Michael addition reaction of 3-substituted oxindoles to protected 2-amino-1-nitroethenes has been developed. The reaction is catalyzed by a simple and readily available amino-indanol derivative and affords the desired products in very high yields (up to 99%) with excellent diastereoselectivities (up to >99:1) and very good enantioselectivities (up to 90%). Significantly, this study provides a general catalytic method for the construction of 3,3′-disubstituted oxindoles bearing α,β- diamino functionality as well as vicinal chiral quaternary/tertiary stereocenters. The potential utility of the protocol also had been demonstrated by gram-scale reaction and the versatile conversion of product. Furthermore, On the basis of the comprehensive experimental results and the absolute configuration of one of the Michael adducts, a work model was also proposed to explain the origin of asymmetric induction.
