Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst

Magnus Rueping; Xiangqian Liu; Teerawut Bootwicha; Roman Pluta; Carina Merkens

doi:10.1039/c3cc49877h

Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst

Magnus Rueping^*, Xiangqian Liu, Teerawut Bootwicha, Roman Pluta, Carina Merkens

^*Corresponding author for this work

Physical Science and Engineering

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

97 Scopus citations

Abstract

The organocatalytic enantioselective trifluoromethylthiolation of oxindoles employing N-(trifluoromethylthio)phthalimide as a stable, easy to handle CF₃S-source has been developed. Optically active products with a quaternary stereogenic center bearing a CF₃S-group are obtained in good yields and with good to excellent enantioselectivities.

Original language	English (US)
Pages (from-to)	2508-2511
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	19
DOIs	https://doi.org/10.1039/c3cc49877h
State	Published - Mar 7 2014

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c3cc49877h

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title = "Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst",

abstract = "The organocatalytic enantioselective trifluoromethylthiolation of oxindoles employing N-(trifluoromethylthio)phthalimide as a stable, easy to handle CF3S-source has been developed. Optically active products with a quaternary stereogenic center bearing a CF3S-group are obtained in good yields and with good to excellent enantioselectivities.",

author = "Magnus Rueping and Xiangqian Liu and Teerawut Bootwicha and Roman Pluta and Carina Merkens",

year = "2014",

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Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst. / Rueping, Magnus; Liu, Xiangqian; Bootwicha, Teerawut; Pluta, Roman; Merkens, Carina.

In: Chemical Communications, Vol. 50, No. 19, 07.03.2014, p. 2508-2511.

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

TY - JOUR

T1 - Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst

AU - Rueping, Magnus

AU - Liu, Xiangqian

AU - Bootwicha, Teerawut

AU - Pluta, Roman

AU - Merkens, Carina

PY - 2014/3/7

Y1 - 2014/3/7

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Catalytic enantioselective trifluoromethylthiolation of oxindoles using shelf-stable N-(trifluoromethylthio)phthalimide and a cinchona alkaloid catalyst

Abstract

ASJC Scopus subject areas

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