Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors

Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser

doi:10.1039/C9OB01134J

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Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors†

Michael Winter,^a Kirill Faust,^b Markus Himmelsbach

^c and Mario Waser

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria
E-mail: Mario.waser@jku.at

^b Institute of Catalysis, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria

^c Institute of Analytial Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria

Abstract

We herein report the first formal (3 + 2)-cyclisation between 3,3,3-trifluoropyruvate-derived imines and indandione-based Michael acceptors. This reaction gives access to a novel class of spirocyclic α-CF₃-α-proline derivatives with complete control of the diastereoselectivity under phase transfer-catalysed reaction conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01134J
Article type: Paper
Submitted: 15 May 2019
Accepted: 24 May 2019
First published: 24 May 2019
This article is Open Access

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Org. Biomol. Chem., 2019,17, 5731-5735

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Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors

M. Winter, K. Faust, M. Himmelsbach and M. Waser, Org. Biomol. Chem., 2019, 17, 5731 DOI: 10.1039/C9OB01134J

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Organic & Biomolecular Chemistry