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Synthesis 2015; 47(11): 1534-1546
DOI: 10.1055/s-0034-1380548
DOI: 10.1055/s-0034-1380548
short review
Synthesis of Fluorinated and Trifluoromethyl-Substituted Alkenes through the Modified Julia Olefination: An Update
Further Information
Publication History
Received: 28 January 2015
Accepted after revision: 19 March 2015
Publication Date:
16 April 2015 (online)
Dedicated to Professor Patrick Rollin on the occasion of his 70th birthday.
Abstract
The modified Julia olefination is now a powerful tool for the synthesis of a large range of functionalized alkenes. This short review covers the last five years and provides an overview of the synthesis of mono-, difluoro-, and trifluoromethyl-substituted alkenes via the modified Julia olefination focusing on the novel scope of this reaction.
1 Introduction
2 Monofluoroalkenes
2.1 Disubstituted α- and β-Monofluoroalkenes
2.2 Bis(trifluoromethyl)phenyl Sulfones
2.3 Conjugated Monofluoroalkenes
2.4 Intramolecular Julia Olefination
2.5 Smiles Rearrangement from Fluorinated Keto Sulfones
2.6 Fluoroallylamines
2.7 Fluorinated exo-Glycals
2.8 Monofluoroalkenes with an α-Stereocenter at the Allylic Position
3 1,1-Difluoroalkenes
4 Trifluoromethyl-Substituted Alkenes
5 Conclusion
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