Abstract
An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent yields with excellent diastereoselectivities and enantioselectivities (up to 98% yield, >20:1 dr and >99% ee). What's more, good yield and high stereoselectivities were obtained in the gram-scale reaction.
Original language | English |
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Pages (from-to) | 7182-7191 |
Number of pages | 10 |
Journal | Organic and Biomolecular Chemistry |
Volume | 17 |
Issue number | 30 |
DOIs | |
Publication status | Published - 2019 |
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Zhang, Q. D., Zhao, B. L., Li, B. Y., & Du, D. M. (2019). Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines. Organic and Biomolecular Chemistry, 17(30), 7182-7191. https://doi.org/10.1039/c9ob01350d