Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome

Chen Xie; Wanxing Sha; Yi Zhu; Jianlin Han; Vadim A. Soloshonok; Yi Pan

doi:10.1039/C6RA27710A

Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome†

Chen Xie,^a Wanxing Sha,^a Yi Zhu,^a Jianlin Han,

*^a Vadim A. Soloshonok^bc and Yi Pan^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, China
E-mail: hanjl@nju.edu.cn

^b Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizabal 3, 20018 San Sebastián, Spain
E-mail: vadym.soloshonok@ehu.es

^c IKERBASQUE, Basque Foundation for Science Department, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain

Abstract

Reported herein is a new approach for the preparation of enantiomerically pure α-fluoro-β-amino-indolin-2-ones possessing tetrasubstituted fluorinated stereogenic centers. This method includes the detrifluoroacetylative in situ generation of tertiary enolates followed by Mannich reaction with (S_s)-sulfinylimines. The operationally convenient conditions coupled with perfect diastereoselectivity and functional substituent compatibility bode well for widespread application of this new synthetic method.

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DOI: https://doi.org/10.1039/C6RA27710A
Article type: Paper
Submitted: 03 Dec 2016
Accepted: 27 Dec 2016
First published: 17 Jan 2017
This article is Open Access

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RSC Adv., 2017,7, 5679-5683

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Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome

C. Xie, W. Sha, Y. Zhu, J. Han, V. A. Soloshonok and Y. Pan, RSC Adv., 2017, 7, 5679 DOI: 10.1039/C6RA27710A

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Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome†

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Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome

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