Abstract
The development of a Michael/cyclization cascade reaction between 3-isothiocyanato-oxindoles and maleimide catalyzed by chrial squaramides is reported. This protocol provides a series of pyrrolidonyl spirooxindoles bearing three contiguous stereocenters in excellent yields (up to 99 %) with high diastereo- and enantioselectivities (up to >99:1 dr, 91 % ee).
Original language | English |
---|---|
Pages (from-to) | 4711-4718 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
Issue number | 27 |
DOIs | |
Publication status | Published - Sept 2016 |
Keywords
- Asymmetric catalysis
- Cascade reactions
- Cyclization
- Michael addition
- Nitrogen heterocycles
- Spiro compounds
Fingerprint
Dive into the research topics of 'Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles'. Together they form a unique fingerprint.Cite this
Liu, L., Zhao, B. L., & Du, D. M. (2016). Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles. European Journal of Organic Chemistry, 2016(27), 4711-4718. https://doi.org/10.1002/ejoc.201600658