Use light instead of acids: Silylenolethers derived from aldehydes and ketones as well as aldehydes themselves react efficiently to give acetals in good to excellent yields. The substrate range with respect to both aldehydes and alcohols i...
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Asymmetric Rubottom‐Type Oxidation Catalyzed by Chiral Calcium Phosphates
Von Wiley-VCH zur Verfügung gestellt
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).
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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