N-Trifluoromethylthiophthalimide: A Stable Electrophilic SCF3-Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation†
Teerawut Bootwicha
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorXiangqian Liu
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorRoman Pluta
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorDr. Iuliana Atodiresei
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Magnus Rueping
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)===Search for more papers by this authorTeerawut Bootwicha
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorXiangqian Liu
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorRoman Pluta
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorDr. Iuliana Atodiresei
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Magnus Rueping
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany)===Search for more papers by this authorX.L. gratefully acknowledges the Chinese Scholarship Council for a fellowship. The absolute configuration was determined by I.A.
Graphical 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.
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