A diversity oriented clicking strategy: the stereoselective synthesis of highly-functionalised olefins from 2-substituted-alkynyl-1-sulfonyl fluorides. Issue 80 (21st September 2022)

• Record Type: Journal Article
• Authors: Smedley, Christopher J.
• Is Part Of: Chemical communications. Volume 58:Issue 80(2022)
• Page Start: 11316
• Page End: 11319
• Publication Date: 2022-09-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc04473k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A novel series of addition reactions for the synthesis of two highly-functionalised sulfonyl fluoride containing olefins from 2-substituted-alkynyl-1-sulfonyl fluorides using a diversity oriented clicking strategy. Abstract : A novel series of addition reactions of highly reactive 2-substituted-alkynyl-1-sulfonyl fluoride (SASF) hubs with DMSO and DMF for the synthesis of two unique sulfonyl fluoride cores is described. The stereoselective chemistry allowed the unprecedented syntheses of 12 ( Z )-2-(dimethylsulfonio)-2-(fluorosulfonyl)-1-substitutedethen-1-olates and 10 ( E )-1-(dimethylamino)-3-oxo-3-substitutedprop-1-ene-2-sulfonyl fluorides from DMSO and DMF, respectively. The reactions proceed expediently to give single products in excellent yield without the need for chromatographic purification. Furthermore, the utility of the DMSO derived products is demonstrated in the synthesis of synthetically valuable β-keto sulfonyl fluorides under hydrogenation conditions in excellent yields.