Asymmetric Rubottom-Type Oxidation Catalyzed by Chiral Calcium Phosphates

Hualing He; K S Satyanarayana Tummalapalli; Linfei Zhu; Minglei Chen; Suvratha Krishnamurthy; Jon C Antilla

doi:10.1002/chem.202203720

Asymmetric Rubottom-Type Oxidation Catalyzed by Chiral Calcium Phosphates

Chemistry. 2023 Feb 16;29(10):e202203720. doi: 10.1002/chem.202203720. Epub 2023 Jan 20.

Authors

Hualing He¹, K S Satyanarayana Tummalapalli¹, Linfei Zhu¹, Minglei Chen¹, Suvratha Krishnamurthy¹, Jon C Antilla¹

Affiliation

¹ Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang Province, 310018, P. R. China.

PMID: 36541518
DOI: 10.1002/chem.202203720

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.

Keywords: Rubottom oxidation; asymmetric hydroxylation; chiral calcium phosphate; meta-chloroperbenzoic acid.