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

Chandra M.R. Volla; Arindam Das; Iuliana Atodiresei; Magnus Rueping

doi:10.1039/c4cc03229b

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

Chandra M.R. Volla, Arindam Das, Iuliana Atodiresei, Magnus Rueping^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

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.

Original language	English (US)
Pages (from-to)	7889-7892
Number of pages	4
Journal	CHEMICAL COMMUNICATIONS
Volume	50
Issue number	58
DOIs	https://doi.org/10.1039/c4cc03229b
State	Published - Jun 24 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Fluorine effects in organocatalysis – asymmetric Br{\o}nsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group",

abstract = "An efficient Br{\o}nsted 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.",

author = "Volla, {Chandra M.R.} and Arindam Das and Iuliana Atodiresei and Magnus Rueping",

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language = "English (US)",

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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. / Volla, Chandra M.R.; Das, Arindam; Atodiresei, Iuliana et al.
In: CHEMICAL COMMUNICATIONS, Vol. 50, No. 58, 24.06.2014, p. 7889-7892.

Research output: Contribution to journal › Article › peer-review

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