43122-40-3Relevant academic research and scientific papers
Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides
Craven, Gregory B.,Briggs, Edward L.,Zammit, Charlotte M.,McDermott, Alexander,Greed, Stephanie,Affron, Dominic P.,Leinfellner, Charlotte,Cudmore, Hannah R.,Tweedy, Ruth R.,Luisi, Renzo,Bull, James A.,Armstrong, Alan
, p. 7403 - 7424 (2021/06/25)
Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late-stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.
An Efficient Protecting-Group-Free Synthesis of Vinylic Sulfoximines via Horner-Wadsworth-Emmons Reaction
Chinthakindi, Praveen K.,Nandi, Ganesh Chandra,Govender, Thavendran,Kruger, Hendrik G.,Naicker, Tricia,Arvidsson, Per I.
, p. 1423 - 1427 (2016/05/24)
Herein, we report a convenient synthesis of aryl-substituted (E)-vinylic NH-sulfoximines via the Horner-Wadsworth-Emmons reaction without the use of protection-deprotection group strategies.
Stereospecific synthesis of N-acyl-(E)-vinyl-, dienyl-, and enynylsulfoximines
Paley,Snow
, p. 5853 - 5856 (2007/10/02)
A β-tosylvinylsulfoximine, 5, was used as the common starting point for the preparation of the title compounds. Treatment of 5 with 'higher-order cuprates' or trialkylalanes (with a Pd(II) catalyst) afforded N-TBDMS-(E)-vinylsulfoximines, whereas dienylsu
