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Issue 23, 2019
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Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors

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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.

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

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Publication details

The article was received on 15 May 2019, accepted on 24 May 2019 and first published on 24 May 2019


Article type: Paper
DOI: 10.1039/C9OB01134J
Org. Biomol. Chem., 2019,17, 5731-5735
  • Open access: Creative Commons BY-NC license
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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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