Trimethylsulfoxonium iodide

About: Trimethylsulfoxonium iodide is a research topic. Over the lifetime, 45 publications have been published within this topic receiving 1440 citations.

Formal [4 + 1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles.

Abstract: A formal [4 + 1] annulation of readily available α-arylhydrazonoketones and trimethylsulfoxonium iodide in the presence of cesium carbonate is described involving a sequential Corey–Chaykovsky reaction and intramolecular nucleophilic cyclization process. Substituted pyrazoles were obtained exclusively from the reactions of α-arylhydrazono-β-oxo-amides and trimethylsulfoxonium iodide in moderate to good yields, whereas the reactions of α-arylhydrazono-β-oxo-ketone/α-arylhydrazono- β-oxo-ester afforded the corresponding dihydropyrazoles in good yields.

Enantioselective Synthesis of 2-(2-Arylcyclopropyl)glycines: Conformationally Restricted Homophenylalanine Analogs

Abstract: Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields Cyclopropanation of the CC bond with trimethylsulfoxonium iodide (Me3SO+I−) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90–97% yields Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stereoselective reduction of the CN bond followed by separation of the formed diastereoisomers, furnished (2-arylcyclopropyl)(furan-2-yl)methanamines 6 in optically pure form and high yield Oxidation of the furan ring of (S,S,S)-, (S,R,R)-, (R,S,S)-, and (R,R,R)-6a afforded the four stereoisomers of α-(2-phenylcyclopropyl) glycine (1a)

A Convenient Synthesis of 2,3-Dihydro-3-methylidene-1H-isoindol-1-ones by Reaction of 2-Formylbenzo­nitriles with Dimethyloxosulfonium Methylide

Abstract: A facile method for the synthesis of 2,3-dihydro-3-methylidene-1H-isoindol-1-one and its derivatives carrying substituent(s) at C(5) and/or C(6) has been developed. The reaction of 2-formylbenzonitrile (1a) with dimethyloxosulfonium methylide, generated by the treatment of trimethylsulfoxonium iodide with NaH in DMSO/THF at 0°, resulted in the formation of 2,3-dihydro-3-methylidene-1H-isoindol-1-one (2a) in 77% yield. Similarly, six 2-formylbenzonitriles carrying substituent(s) at C(4) and/or C(5), i.e., 1b–1g, also gave the corresponding expected products 2b–2g in comparable yields.