Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines

Alejandra Riesco-Domínguez, Jeroen Van De Wiel, Trevor A. Hamlin, Bas Van Beek, Stephen D. Lindell, Daniel Blanco-Ania, F. Matthias Bickelhaupt*, Floris P.J.T. Rutjes

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.

Original languageEnglish
Pages (from-to)1779-1789
Number of pages11
JournalJournal of Organic Chemistry
Volume83
Issue number4
Early online date10 Jan 2018
DOIs
Publication statusPublished - 16 Feb 2018

Funding

This work has been supported by the FP7Marie Curie Actions of the European Commission via the ITN ECHONET Network (MCITN-2012-316379) and NWO via the Planetary and Exoplanetary Science program (PEPSci) and the Dutch Astrochemistry Network (DAN). We thank Dr. Paul B. White for his help in the assignment of the diastereo-and regioisomers, and Birgit Kuhn (Bayer AG) for the helpful discussions.

FundersFunder number
Dutch Astrochemistry Network
FP7Marie Curie Actions of the European Commission
ITN ECHONET NetworkMCITN-2012-316379
Seventh Framework Programme316379
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

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