- Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
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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.
- Baggerman, Jacob,Jordaan, Daan,Liang, Dong-Dong,Streefkerk, Dieuwertje E.,Wagemakers, Jorden,Zuilhof, Han
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p. 7494 - 7500
(2020/03/23)
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- Direct Synthesis of N-Acyl Sulfonimidamides and N-Sulfonimidoyl Amidines from Sulfonimidoyl Azides
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Herein, we describe the preparation of sulfonimidoyl azides, and demonstrate their utility in the construction of N-acyl sulfonimidamides and N-sulfonimidoyl amidines. N-Acyl sulfonimidamides were synthesized in good to very good yields via “on water” cop
- Nandi, Ganesh Chandra,Jesin, Irfana
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supporting information
p. 2465 - 2469
(2018/05/30)
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- Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides
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N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF3) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.
- Kowalczyk, Rafal,Edmunds, Andrew J. F.,Hall, Roger G.,Bolm, Carsten
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p. 768 - 771
(2011/04/24)
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- Synthesis of amino-functionalized sulfonimidamides and their application in the enantioselective henry reaction
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Amino-functionalized sulfonimidamides have been prepared by aziridinium ring-opening reactions and nucleophilic substitutions of sulfonimidoyl chlorides. Whereas the former reactions afford separable diastereomeric products, the latter provide single ster
- Steurer, Marianne,Bolm, Carsten
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experimental part
p. 3301 - 3310
(2010/08/19)
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