Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines

Qing Da Zhang, Bo Liang Zhao, Bing Yu Li, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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 languageEnglish
Pages (from-to)7182-7191
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number30
DOIs
Publication statusPublished - 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