Davis, Franklin A.; Weismiller, Michael C.; Murphy, Christopher K.; Reddy, R. Thimma; Chen, Band Chi published the artcile< Chemistry of oxaziridines. 18. Synthesis and enantioselective oxidations of the [(8,8-dihalocamphoryl)sulfonyl]oxaziridines>, HPLC of Formula: 104322-63-6, the main research area is oxaziridine camphorsulfonyl chem reaction; enantioselective oxidation dihalocamphorylsulfonyloxaziridine sulfide; sulfoxide chiral; camphorylsulfonylimine halogenation chlorination bromination fluorination; halocamphorylsulfonylimine preparation halogenation epoxidation; epoxidation dihalocamphorylsulfonyloxaziridine oxone chloroperbenzoic acid; asym oxidation sulfide dihalocamphorylsulfonyloxaziridine; mol recognition oxidation sulfide dihalocamphorylsulfonyloxaziridine; steric interaction oxidation sulfide dihalocamphorylsulfonyloxaziridine; electronic effect oxidation sulfide dihalocamphorylsulfonyloxaziridine; transition state structure oxidation sulfide dihalocamphorylsulfonyloxaziridine; hydroxylation asym enolate dihalocamphorylsulfonyloxaziridine.
The synthesis and enantioselective oxidations of [(8,8-dihalocamphoryl)sulfonyl]oxaziridines I (R = F, Cl, Br) are reported. These reagents are prepared in two steps from the (camphorylsulfonyl)imine II (R1 = R2 = H) by treatment of the corresponding azaenolate with electrophilic halogen sources followed by biphasic oxidation of the resulting dihaloimine II (R1 = R2 = F; R1 = R2 = Cl; R1 = R2 = Br) with m-CPBA/K2CO3. Of these oxaziridines the dichloro reagent I (R = Cl), available on a multigram scale, affords the highest enantioselectivities for the asym. oxidation of sulfides to sulfoxides (42-74%) and for the hydroxylation of enolates (often better than 95% ee). In general the mol. recognition is predicted and explained in terms of minimization of nonbonded steric interactions in the transition states. For the asym. oxidation of sulfides to sulfoxides, secondary electronic factor related to the polarity of the sulfide and oxaziridine also play a role. Definitive evidence for chelation of the metal enolate with the C-X bond in I (R = F, Cl, Br) is not found. The mol. recognition is interpreted in terms of the higher reactivity of the reagents and an active-site structure which is sterically complementary with the enolate. For the asym. hydroxylation of the Z- and E-enolates of propiophenone, EtCOPh, the Z-enolate exhibits much higher stereoselectivity than the E-enolate: >95% vs 22% ee.
Journal of Organic Chemistry published new progress about Hydroxylation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, HPLC of Formula: 104322-63-6.
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com