95841-50-2Relevant articles and documents
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.
Regio- and stereospecific cleavage of stannylepoxides with lithium phenylsulfide
Cuadrado, Purificación,González-Nogal, Ana M.
, p. 8993 - 8996 (2007/10/03)
Unsubstituted and α or β C-substituted epoxystannanes react with lithium phenylsulfide to give regio- and stereodefined α-phenylthio-β-hydroxystannanes resulting from α-opening with inversion of configuration. On the other hand, α- or β-trans-silyl epoxys
Synthesis of Triafulvalene Precursors by 'Carbene-Dimerization' of 1-Halogeno-1-lithiocyclopropanes
Laeng, Christoph,Muehlebach, Michel,Neuenschwander, Markus
, p. 2124 - 2136 (2007/10/03)
Bi(cyclopropylidenes) 7a, 7c, and 7e are available in a simple one-pot reaction by treating 1,1-dibromocyclopropanes 5 at -95° with BuLi and CuCl2. Attempts towards triafulvalene precursors with good leaving groups are reported. The most promising attempt makes use of 2,2′-bis(phenylthio)-3.3′-bis(trimethylsilyl)-1.1′- bi(cyclopropylidene) (7c) which has been oxidized to give the bis(phenylsulfonyl) derivative 7g. So far, F--induced elimination experiments with 7g failed.
