Issue 30, 2019
From the journal:

Organic & Biomolecular Chemistry

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

Qing-Da Zhang,a   Bo-Liang Zhao,a   Bing-Yu Lia  and  Da-Ming Du ORCID logo *a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China
E-mail: dudm@bit.edu.cn
Web: http://scc.bit.edu.cn/

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.

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

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Article information

DOI
https://doi.org/10.1039/C9OB01350D
Article type
Paper
Submitted
14 Jun 2019
Accepted
09 Jul 2019
First published
09 Jul 2019

Org. Biomol. Chem., 2019,17, 7182-7191

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

Q. Zhang, B. Zhao, B. Li and D. Du, Org. Biomol. Chem., 2019, 17, 7182 DOI: 10.1039/C9OB01350D

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