Issue 23, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 May 2019
Accepted
24 May 2019
First published
24 May 2019
This article is Open Access
Creative Commons BY-NC license

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

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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