Issue 58, 2014

Fluorine effects in organocatalysis – asymmetric Brønsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group

Abstract

An efficient Brønsted acid assisted Lewis base catalysis protocol for the synthesis of enantiomerically pure trifluoromethylated dihydropyridazines starting from readily available hydrazones and α,β-unsaturated aldehydes has been developed. The reaction exhibits high tolerance towards many functional groups and is applicable to various aliphatic, aromatic and hetero-aromatic α,β-unsaturated aldehydes, and provides the products in good yields and with excellent enantioselectivities.

Graphical abstract: Fluorine effects in organocatalysis – asymmetric Brønsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group

Supplementary files

Article information

Article type
Communication
Submitted
30 Apr 2014
Accepted
19 May 2014
First published
09 Jun 2014

Chem. Commun., 2014,50, 7889-7892

Author version available

Fluorine effects in organocatalysis – asymmetric Brønsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group

C. M. R. Volla, A. Das, I. Atodiresei and M. Rueping, Chem. Commun., 2014, 50, 7889 DOI: 10.1039/C4CC03229B

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