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, Kirill Faust, Markus Himmelsbach and Mario Waser
Org. Biomol. Chem., 2019,17, 5731-5735
DOI: 10.1039/C9OB01134J, Paper

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Abstract | Cited by

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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