Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope,Enantioselectivity, and Mechanism |
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| Authors: | Dr. Dong-Dong Liang Dieuwertje E. Streefkerk Daan Jordaan Jorden Wagemakers Dr. Jacob Baggerman Prof. Dr. Han Zuilhof |
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| Affiliation: | 1. Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The Netherlands These authors contributed equally to this work.;2. Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE Wageningen, The Netherlands |
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| Abstract: | SuFEx reactions, in which an S−F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, “Si-free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products. |
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| Keywords: | Enantioselektivität Reaktionskinetik Reaktionsmechanismen SuFEx |
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