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- Title
Diastereo- and Enantioselective Michael Addition of 3-Substituted Oxindoles to Trifluoromethyl-Substituted Nitro Olefins Catalyzed by a Cinchona-Alkaloid-Derived Squaramide.
- Authors
Zhao, Mei‐Xin; Ji, Fei‐Hu; Zhao, Xiao‐Li; Han, Ze‐Zheng; Shi, Min
- Abstract
Highly efficient diastereo- and enantioselective Michael addition reactions between 3-substituted oxindoles and trifluoromethylated nitro olefins catalyzed by a quinine-derived squaramide have been investigated. The corresponding adducts, each bearing a chiral tertiary carbon center attached to a trifluoromethyl group and adjacent to a quaternary stereocenter at the C3 position of the oxindole, were obtained in good to excellent yields (up to 99 %) and with high diastereoselectivities (up to >20:1 dr) and excellent enantioselectivities (up to 99 % ee).
- Subjects
OXINDOLES; INDOLINE; TRIFLUOROMETHYL compounds; NITROALKENES; CINCHONA
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 3, p644
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301457