Development of C-6′-modified quinine-derived phase-transfer catalysts and their application in the enantioselective α-hydroxylation of β-dicarbonyl compounds

An efficient quinidine-based phase-transfer-catalyzed enantioselective cascade oxa-Michael-cyclization reaction of hydroxylamine with various β-carboxy-substituted α,β-unsaturated ketones has been achieved for the preparation of chiral carboxy-substituted 2-isoxazolines. This cascade reaction provided the desired products in good yields (up to 98%) with excellent enantioselectivities (91-96% ee). In addition, the cascade reaction was effectively applied to the first catalytic asymmetric synthesis of the herbicide (S)-methiozolin.

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Asymmetric bis(oxazoline)–Ni(ii) catalyzed α-hydroxylation of cyclic β-keto esters under visible light

Yin

Wang

Zhao

et al. 2021

Org. Biomol. Chem.

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Development of C-6′-modified quinine-derived phase-transfer catalysts and their application in the enantioselective α-hydroxylation of β-dicarbonyl compounds

Cited by 6 publications

References 19 publications

Desymmetrization of 2‐Cyano‐N‐tosylbenzylidenimine with Thiols and Organocatalytic Heterocyclization by Dynamic Resolution: Mechanism Investigation

Desymmetrization of 2‐Cyano‐N‐tosylbenzylidenimine with Thiols and Organocatalytic Heterocyclization by Dynamic Resolution: Mechanism Investigation

Catalytic enantioselective synthesis of carboxy-substituted 2-isoxazolines by cascade oxa-Michael-cyclization

Asymmetric bis(oxazoline)–Ni(ii) catalyzed α-hydroxylation of cyclic β-keto esters under visible light

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