[EN] PROCESS FOR THE PREPARATION OF HETEROARYL-SUBSTITUTED SULFUR(VI) COMPOUNDS [FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DU SOUFRE (VI) SUBSTITUÉS PAR UN HÉTÉROARYLE
Iron(II)-mediated Nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals
作者:Thorsten Bach、Christina Korber
DOI:10.1016/s0040-4039(98)00927-7
日期:1998.7
nitrene transfer from t-Butyloxycarbonyl azide (BocN3) to several nucleophiles is promoted by ferrous chloride (FeCl2) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or a-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH2C12 as solvent the FeCl2-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was
2-Sulfonimidoylylidene tetrahydrofurans and 2-sulfonimidoylylidene-5-vinyl tetrahydrofurans were readily synthesized via a consecutive acylation/SN2 sequence with total regio- and chemoselectivity from Johnson's sulfoximine derivatives. The same consecutive reaction could also be applied to the expeditious synthesis of 6-sulfonimidoylmethyl-3,4-dihydro-2H-pyrans. (C) 2009 Elsevier Ltd. All rights reserved.
The Preparation ofN-tert-Butyloxycarbonyl-(Boc-)Protected Sulfoximines and Sulfimines by an Iron(II)-Mediated Nitrene Transfer from BocN3 to Sulfoxides and Sulfides
yield). The sterospecificity of the reaction was demonstrated with the enantiomerically enriched substrates (R)-(+)-1b and (S)-(–)-1d which yielded the sulfoximides (R)-(+)-3b and (S)-(–)-3d with retention of configuration. Mechanistically, an intermediate (nitrene)FeIV complex is postulated as the reactive nitrenetransfer reagent which is formed from FeCl2 and BocN3. The more nucleophilic sulfides 2 reacted
[EN] PROCESS FOR THE PREPARATION OF HETEROARYL-SUBSTITUTED SULFUR(VI) COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS DU SOUFRE (VI) SUBSTITUÉS PAR UN HÉTÉROARYLE
申请人:H LEE MOFFITT CANCER CT & RES
公开号:WO2022094218A1
公开(公告)日:2022-05-05
The present disclosure provides processes for the synthesis of organic compounds, in particular processes for the synthesis of heteroaryl-substituted sulfur(VI) compounds by nucleophilic aromatic substitution.