Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

文献情報

出版日 2020-04-17

DOI 10.1039/D0QO00348D

インパクトファクター 5.281

著者

Luyao Li, Bo Zhu, Huihui Fan, Zhiyong Jiang, Junbiao Chang

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要旨

Herein, we report a chiral bifunctional thiourea catalyzed asymmetric Michael addition reaction between 2-(trifluoromethyl)oxazol-5(2H)-one as a direct C-2-position nucleophile and 4-nitro-5-styrylisoxazoles for the first time. The reaction affords the corresponding products bearing adjacent CF3-substituted hetero-quaternary and tertiary stereocenters in moderate to high yields (up to 94% yield) with good to excellent enantioselectivities (up to 99% ee) and excellent diastereoselectivities (up to >20 : 1 dr) under mild reaction conditions. Moreover, the selected compounds displayed good biological activities and further investigation is underway.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

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