Asymmetric Rubottom-Type Oxidation Catalyzed by Chiral Calcium Phosphates
Hualing He1, K S Satyanarayana Tummalapalli1, Linfei Zhu1
1Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang Province, 310018, P. R. China.
Abstract:
A highly efficient catalytic asymmetric Rubottom-type oxidation is described. Using meta-chloroperbenzoic acid (m-CPBA) as the oxidant and chiral calcium phosphate as the catalyst, the facile transformation enables direct hydroxylation of N-Boc oxindoles and β-ketoesters in high yields (up to 99 %) and in a highly enantioenriched fashion (up to >99 % ee). The application of the established method was demonstrated by the synthesis of a pharmaceutically important 3-hydroxyoxindole with excellent enantiocontrol.
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