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

doi:10.1021/acs.joc.7b02639

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

AIMMS

Research output: Contribution to Journal › Article › Academic › peer-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 language	English
Pages (from-to)	1779-1789
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	83
Issue number	4
Early online date	10 Jan 2018
DOIs	https://doi.org/10.1021/acs.joc.7b02639
Publication status	Published - 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.

Funders	Funder number
Dutch Astrochemistry Network
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Planetary and Exoplanetary Science program
European Commission
FP7Marie Curie Actions of the European Commission
ITN ECHONET Network	MCITN-2012-316379
Seventh Framework Programme	316379

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 6 Clean Water and Sanitation

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10.1021/acs.joc.7b02639

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Cite this

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title = "Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines",

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.",

author = "Alejandra Riesco-Dom{\'i}nguez and \{Van De Wiel\}, Jeroen and Hamlin, \{Trevor A.\} and \{Van Beek\}, Bas and Lindell, \{Stephen D.\} and Daniel Blanco-Ania and Bickelhaupt, \{F. Matthias\} and Rutjes, \{Floris P.J.T.\}",

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AU - Hamlin, Trevor A.

AU - Van Beek, Bas

AU - Lindell, Stephen D.

AU - Blanco-Ania, Daniel

AU - Bickelhaupt, F. Matthias

AU - Rutjes, Floris P.J.T.

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AB - 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.

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