N-trifluoromethylthiophthalimide: A stable electrophilic SCF 3-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation

Teerawut Bootwicha; Xiangqian Liu; Roman Pluta; Iuliana Atodiresei; Magnus Rueping

doi:10.1002/anie.201304957

N-trifluoromethylthiophthalimide: A stable electrophilic SCF ₃-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation

Teerawut Bootwicha, Xiangqian Liu, Roman Pluta, Iuliana Atodiresei, Magnus Rueping^*

^*Corresponding author for this work

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

242 Scopus citations

Abstract

Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF₃ source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF₃ esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF₃ β-hydroxyesters.

Original language	English (US)
Pages (from-to)	12856-12859
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	49
DOIs	https://doi.org/10.1002/anie.201304957
State	Published - Dec 2 2013
Externally published	Yes

Keywords

cinchona alkaloids
fluorine
indanones
organocatalysis
trifluoromethylsulfenylation

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201304957

Cite this

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title = "N-trifluoromethylthiophthalimide: A stable electrophilic SCF 3-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation",

abstract = "Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF3 β-hydroxyesters.",

keywords = "cinchona alkaloids, fluorine, indanones, organocatalysis, trifluoromethylsulfenylation",

author = "Teerawut Bootwicha and Xiangqian Liu and Roman Pluta and Iuliana Atodiresei and Magnus Rueping",

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T2 - A stable electrophilic SCF 3-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation

AU - Bootwicha, Teerawut

AU - Liu, Xiangqian

AU - Pluta, Roman

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

PY - 2013/12/2

Y1 - 2013/12/2

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AB - Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF3 β-hydroxyesters.

KW - cinchona alkaloids

KW - fluorine

KW - indanones

KW - organocatalysis

KW - trifluoromethylsulfenylation

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