Abstract
A squaramide-catalyzed asymmetric Mannich reaction of 3-fluorooxindoles to isatin-derived imines for synthesis of fluorinated 3,3′-bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′-bisoxindoles were obtained in excellent yields with excellent diastereo- and enantioselectivities (up to 99% yield, >99:1 dr and >99% ee). What's more, this reaction can be gram-scaled without compromising yield and stereoselectivity. (Figure presented.).
Original language | English |
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Pages (from-to) | 3164-3170 |
Number of pages | 7 |
Journal | Advanced Synthesis and Catalysis |
Volume | 360 |
Issue number | 16 |
DOIs | |
Publication status | Published - 17 Aug 2018 |
Keywords
- Asymmetric catalysis
- Bisoxindoles
- Mannich addition
- Organocatalysis
- Squaramides
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Li, B. Y., & Du, D. M. (2018). Chiral Squaramide-Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3′-Bisoxindoles. Advanced Synthesis and Catalysis, 360(16), 3164-3170. https://doi.org/10.1002/adsc.201800513