80684-96-4Relevant academic research and scientific papers
Stereoselective Reaction of α-Sulfinyl Carbanion Derived from Chiral 2-(Trialkylsilyl)ethyl Sulfoxides: Evidence for a Novel Silicon - Oxygen Interaction
Nakamura, Shuichi,Takemoto, Hirofumi,Ueno, Yoshio,Toru, Takeshi,Kakumoto, Terumitsu,Hagiwara, Tsuneo
, p. 469 - 474 (2007/10/03)
Reactions of α-sulfinyl carbanions, derived from p-tolyl sulfoxides bearing various alkyl groups, with various electrophiles were examined. The reaction of α-sulfinyl carbanions, derived from the β-silylethyl sulfoxides, with ketones or trimethyl phosphate, gave the syn products with high stereoselectivity. Interaction between the silicon in the trialkylsilyl group and the carbonyl oxygen in nucleophiles was postulated to stabilize the transition state, leading preferably to the syn diastereisomers. This novel silicon-oxygen interaction was supported by an MO calculation study using the MOPAC 93/PM3 and the Gaussian 94 Beche3LYP/3-21+G* methods.
Enantio- and Diastereoselectivity in the Periodate Oxidation of Sulfides Catalyzed by Bovine Serum Albumin. 2
Colonna, Stefano,Banfi, Stefano,Annunziata, Rita,Casella, Luigi
, p. 891 - 895 (2007/10/02)
The asymmetric oxidation of aliphatic, aromatic, and heterocyclic sulfides in the presence of a catalytic amount of bovine serum albumin (BSA) affords the corresponding sulfoxides with enantiomeric excess (ee) up to 80percent.The diastereoselectivity of the process has also been examined in comparison with the enzymatic oxygenation with cytochrome P-450.Electronic and CD spectral data indicate that the sulfides are not tightly bound to BSA in the reaction conditions.
Optical Stability of Carbanions Derived from Sulphoximides and Sulphilimines
Annunziata, Rita,Cinquini, Mauro,Colonna, Stefano,Cozzi, Franco
, p. 1005 - 1006 (2007/10/02)
Pairs of diastereomeric sulphoximides and sulphilimines of known absolute configuration have been converted into the corresponding carbanions, which have a definite optical stability.
