494846-92-3Relevant academic research and scientific papers
Synthesis of Highly Enantioenriched Sulfonimidoyl Fluorides and Sulfonimidamides by Stereospecific Sulfur–Fluorine Exchange (SuFEx) Reaction
Greed, Stephanie,Briggs, Edward L.,Idiris, Fahima I. M.,White, Andrew J. P.,Lücking, Ulrich,Bull, James A.
supporting information, p. 12533 - 12538 (2020/09/16)
Sulfonimidamides present exciting opportunities as chiral isosteres of sulfonamides, with potential for additional directional interactions. Here, we present the first modular enantioselective synthesis of sulfonimidamides, including the first stereoselective synthesis of enantioenriched sulfonimidoyl fluorides, and studies on their reactivity. A new route to sulfonimidoyl fluorides is presented from solid bench-stable, N-Boc-sulfinamide (Boc=tert-butyloxycarbonyl) salt building blocks. Enantioenriched arylsulfonimidoyl fluorides are shown to be readily racemised by fluoride ions. Conditions are developed, which trap fluoride and enable the stereospecific reaction of sulfonimidoyl fluorides with primary and secondary amines (100 % es, es=enantiospecificity) generating sulfonimidamides with up to 99 % ee. Aryl and alkyl sulfonimidoyl fluoride reagents are suitable for mild late stage functionalisation reactions, exemplified by coupling with a selection of complex amines in marketed drugs.
Synthesis of amino-functionalized sulfonimidamides and their application in the enantioselective henry reaction
Steurer, Marianne,Bolm, Carsten
experimental part, p. 3301 - 3310 (2010/08/19)
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
Synthesis of enantiopure sulfonimidamides and elucidation of their absolute configuration by comparison of measured and calculated CD spectra and X-ray crystal structure determination
Worch, Christin,Atodiresei, Iuliana,Raabe, Gerhard,Bolm, Carsten
experimental part, p. 677 - 683 (2010/06/19)
Straightforward syntheses of enantiopure N-benzoyl- and N-tert-butyloxycarbonyl-protected sulfonimidamides, which can be used as building blocks in newly designed catalysts, are presented. Key synthetic step is a dynamic resolution of a racemic sulfinic acid sodium salt. All subsequent transformations proceed stereospecifically. The absolute configurations at the sulfur atoms of both sulfonimidamides were determined by comparison of measured and calculated CD spectra. An X-ray crystal structure determination of a sulfonimidoylguanidine derivative confirmed this result.
