189375-92-6Relevant academic research and scientific papers
Diastereoselective Conjugate Additions Reactions of a Lithiated Allylic Sulfoximine to Acyclic Enones
Pyne, Stephen G.,Dong, Zemin,Skelton, Brian W.,White, Allan H.
, p. 751 - 752 (1994)
The conjugate addition reactions of lithiated N-p-tosyl S-phenyl S-prop-2-enyl sulfoximine 4 with cyclic and acyclic enones gives exclusively 1,4-α-adducts, the reactions with acyclic enones are highly diastereoselective.
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.
DIASTEREOSELECTIVE REACTIONS OF ALLYLIC SULFOXIMINE ANIONS
Pyne, Stephen G.,Dong, Zemin
, p. 425 - 426 (2007/10/02)
The conjugate addition reactions of lithiated N-p-tolyl S-phenyl S-2-propenyl sulfoximine (4) with cyclic and acyclic enones gives exclusively 1,4-α adducts, the reactions with acyclic enones are highly diastereoselective.
