Davis, Franklin A.; Sheppard, Aurelia C.; Chen, Bang Chi; Haque, M. Serajul published the artcile< Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine>, Product Details of C10H15NO3S, the main research area is ketone enolate asym oxidation; oxidation stereoselective ketone enolate; asym oxidation enolate chiral oxaziridine; oxidizing agent stereoselective camphorylsulfonyloxaziridine; hydroxy ketone.
The reagent-controlled asym. oxidation of in situ generated RR1C:CR2OX (I; R = H, Me; R2 = Me, CMe3, Ph; X = Na, K, Li) by enantiomerically pure (camphorylsulfonyl)oxaziridines, e.g., (+)-II, has been investigated. The stereoselectivities for oxidation of trisubstituted enolates are good to excellent, 60-95% enantiomeric excess (ee), while those for tetrasubstituted enolates are lower; i.e., 21-30% ee. Isolated chem. yields for both types of enolate anions are good to excellent. The Na enolate anions, which could be oxidized at -78°, gave both higher yields and stereoselectivities than the corresponding Li enolates, which required warming to higher temperatures for complete oxidation The presence of HMPA generally had a deleterious effect on the stereoinduction. However, for oxidation of (E)- and (Z)-I (R = Ph, R1 = H, R2 = Me, X = Na, Li) the highest ee’s were observed in the presence of this additive. Investigation of the stereoselective trends reveals that the enolate substitution pattern and the enolate solution structure are the most important stereocontrol elements. The role that enolate geometry has in the stereoinduction is less clear, although (Z) enolates exhibit higher stereoselectivities than the (E) enolates. The results obtained in this study have been formulated into a mechanistic rational involving an SN2-type substitution of the enolate anion on II via an open transition state.
Journal of the American Chemical Society published new progress about Enolates Role: RCT (Reactant), RACT (Reactant or Reagent). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Product Details of C10H15NO3S.
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com