Davis, Franklin A.; Reddy, G. Venkat; Chen, Bang-Chi; Kumar, Anil; Haque, M. Serajul published the artcile< Enantioselective Synthesis of 2-Methyl-2-hydroxy-γ-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone>, COA of Formula: C10H15NO3S, the main research area is asym hydroxylation methylbutyrolactone phenylisobutyrate; camphorsulfonyloxaziridine chiral auxiliary hydroxylation; frontalin formal asym synthesis; mevalonolactone asym synthesis.
The asym. hydroxylation of the enolates of (R)-menthyl 2-methyl-3-phenylpropionate (I) and 2-methyl-γ-butyrolactone (II) with (camphorylsulfonyl)oxaziridines was studied. The stereoselectivities of the tertiary α-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of I with substoichiometric amounts of (camphorylsulfonyl)oxaziridine, the yields were unsatisfactory. On the other hand, the enantioselective α-hydroxylation of the sodium enolate of II with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine afforded α-hydroxy lactone in 70% yield and 84% ee. The enantiomeric excess was improved to >93% ee by crystallization of the corresponding benzoate. The utility of both enantiomers of the benzoate was demonstrated in the formal asym. synthesis of (1S,5R)-(-)-frontalin and in the asym. synthesis of (R)-(-)-mevalonolactone.
Journal of Organic Chemistry published new progress about Chiral synthons. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, COA of Formula: C10H15NO3S.
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com