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

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Abstract

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.

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

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Publication details

The article was received on 06 Nov 2017, accepted on 29 Dec 2017 and first published on 02 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02722B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Catalytic enantioselective synthesis of carboxy-substituted 2-isoxazolines by cascade oxa-Michael-cyclization

    H. Lee, B. Eun, E. Sung, G. T. Hwang, Y. K. Ko and C. Cho, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02722B

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