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J Org Chem. 2016 Aug 19;81(16):7042-50. doi: 10.1021/acs.joc.6b00856. Epub 2016 Jul 7.

A Series of Cinchona-Derived N-Oxide Phase-Transfer Catalysts: Application to the Photo-Organocatalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds.

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1
State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , No. 2 Linggong Road, Dalian 116024 Liaoning Province, P. R. China.

Abstract

A series of cinchona-derived N-oxide asymmetric phase-transfer catalysts were synthesized and applied in the enantioselective photo-organocatalytic α-hydroxylation of β-keto esters and β-keto amides (23 examples) using molecular oxygen in excellent yields (up to 98%) and high enantioselectivities (up to 83% ee). These new catalysts could be recycled and reused six times for such a reaction with almost the original reactivity and enantioselectivity.

PMID:
27336753
DOI:
10.1021/acs.joc.6b00856

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