Enantioselective Nucleophilic Vinylic Substitution (S N V) toward 3-Alkenyl-bisoxindoles Facilitated by C6' Steric Bulk of Cinchona Alkaloid.
- Resource Type
- Academic Journal
- Authors
- Wang X; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Bai G; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Liu R; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Zhu X; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Ye X; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Zhang T; Shaoxing Minsheng Pharmaceutical Co., Ltd, Shaoxing 312071, China.; Zhang K; Shaoxing Minsheng Pharmaceutical Co., Ltd, Shaoxing 312071, China.; Bonne D; Aix Marseille University, CNRS, Centrale Marseille, iSm2, 13013 Marseille, France.; Rodriguez J; Aix Marseille University, CNRS, Centrale Marseille, iSm2, 13013 Marseille, France.; Wang H; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.; Bao X; College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.
- Source
- Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: PubMed not MEDLINE; MEDLINE
- Subject
- Language
- English
A C6' bulky substituted quinine-catalyzed S N V reaction between 3-substituted oxindole and ( E )-3-(nitromethylene)-oxindole was developed. This enantioselective C( sp 3 )-C( sp 2 ) coupling furnished bisoxindole scaffolds featuring a vinyl-substituted all-carbon quaternary stereocenter with high stereoselectivities. In addition, the gram-scale synthesis and synthetic post-transformations were conducted to demonstrate the potential synthetic usefulness.