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- Title
Squaramide-Catalyzed Synthesis of Enantioenriched Spirocyclic Oxindoles via Ketimine Intermediates with Multiple Active Sites.
- Authors
Sun, Qiang‐Sheng; Zhu, Hua; Chen, Yong‐Jian; Yang, Xiao‐Di; Sun, Xing‐Wen; Lin, Guo‐Qiang
- Abstract
A new method for the construction of five-membered spirocyclic oxindoles is based on a Michael-Mannich cascade reaction of a ketimine intermediated catalyzed by a bifunctional quinine-derived squaramide. The desired products were obtained in excellent yields (up to 94 %) and stereoselectivities (up to >20:1 d.r., >99 % ee). A scaled-up variant also proceeded smoothly showing that the one-pot reaction might find application in the synthesis of bioactive-compound libraries.
- Subjects
OXINDOLES; BINDING sites; ORGANOCATALYSIS; CHEMICAL synthesis; CHEMICAL research
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 45, p13451
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201506206