169137-89-7Relevant articles and documents
An efficient preparation of β-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles
Pesa, Nela,Welch, Chris J.,Boa, Andrew N.
, p. 599 - 607 (2007/10/03)
A simple reaction affording (E)-1-dimethylamino-2-phenylsulfonylethylene, and S-((E)-2-(N′N′-dimethylamino)ethenyl)-5-phenyl-N-(p- tolylsulfonyl) sulfoximide in high yields is described. A reversal in regioselectivity was observed when the ss-dimethylamin
Cyclopropanation reactions of enones with lithiated sulfoximines: Application to the asymmetric synthesis of chiral cyclopropanes
Pyne, Stephen G.,Dong, Zemin,Skelton, Brian W.,White, Allan H.
, p. 2337 - 2343 (2007/10/03)
Stabilized lithiated sulfoximines 2 and 9 undergo highly diastereoselective Michael reactions with acyclic enones under kinetically controlled conditions. At rt the initially formed anionic Michael adducts undergo intramolecular displacement of the sulfonimidoyl group, with inversion of stereochemistry at the carbon bearing the nucleofuge, to give cyclopropanes. Lithiated sulfoximines derived from S-alkyl sulfoximines give mixtures of 1,2- and 1,4-adducts with enones mider kinetically controlled conditions. However, at rt the 1,2-adducts are in equilibrium with their corresponding 1,4-adducts. The 1,4-adducts are formed in a highly diastereoselective manner and are rapidly converted to diastereomerically pure cyclopropanes in good to excellent yields. Optically active versions of these sulfoximines give cyclopropanes in high enantiomeric purities.
Synthesis and Highly Diastereoselective Nucleophilic Epoxidation of N-(p-Tolylsulfonyl)vinylsulfoximines
Bailey, Peter L.,Clegg, William,Jackson, Richard F. W.,Meth-Cohn, Otto
, p. 343 - 350 (2007/10/02)
N-(p-Tolylsulfonyl)vinylsulfoximines 3 may be prepared in good yield in a one-pot process by reaction of lithiated S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfoximine with aldehydes, followed by elimination using methanesulfonyl chloride-triethylamine.The vi
