110332-81-5Relevant academic research and scientific papers
Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: Asymmetric C-N bond formation
Murakami, Masakazu,Katsuki, Tsutomu
, p. 3947 - 3949 (2007/10/03)
Asymmetric C-N bond formation was achieved in a highly enantioselective manner by using (OC)Ru(salen)-catalyzed sulfimidation and the subsequent [2,3]sigmatropic rearrangement: treatment of allyl aryl sulfides with p-toluenesulfonyl azide in the presence of a catalytic amount of (OC)Ru(salen) followed by hydrolysis of the resulting N-allyl-N-arylthio toluenesulfonamides provided N-allyl toluenesulfonamides of high enantiomeric excess.
Catalytic Asymmetric Sulfimidation
Takada, Hiroya,Nishibayashi, Yoshiaki,Ohe, Kouichi,Uemura, Sakae,Baird, Charlotte P.,Sparey, Tim J.,Taylor, Paul C.
, p. 6512 - 6518 (2007/10/03)
A direct catalytic imidation of sulfides to sulfimides with [N-(p-tolylsulfonyl)imino]phenyliodinane (TsN=IPh) using a catalytic amount of copper triflate (CuOTf) has been developed. The reaction proceeds with a wide range of sulfides to give the corresponding sulfimides in 50-83% isolated yields. When the reaction is applied to allylic sulfides, the products are the corresponding sulfonamides produced via [2,3] sigmatropic rearrangement of the initially formed allylic sulfimides. In the presence of a chiral bis(oxazoline) as ligand, asymmetric induction occurs to afford the chiral sulfimides (up to 71% ee) and sulfonamides (up to 58% ee). Chloramine T (TsNClNa) can be used in place of TsN=IPh for asymmetric sulfimidation, but the ee's are much lower. Some mechanistic observations are described.
Novel asymmetric catalytic synthesis of sulfimides
Takada, Hiroya,Nishibayashi, Yoshiaki,Ohe, Kouichi,Uemura, Sakae
, p. 931 - 932 (2007/10/03)
Prochiral sulfides react with PhI=NTs in the presence of a catalytic amount of Cu1 salt together with chiral 4,4′-disubstituted bis(oxazoline) ligands to afford the corresponding chiral sulfimides.
