Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines.

Zhang, Qing-Da; Zhao, Bo-Liang; Li, Bing-Yu; Du, Da-Ming

Zhang, Qing-Da; Zhao, Bo-Liang; Li, Bing-Yu; Du, Da-Ming.

Afiliación

Zhang QD; School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China. dudm@bit.edu.cn.
Zhao BL; School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China. dudm@bit.edu.cn.
Li BY; School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China. dudm@bit.edu.cn.
Du DM; School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China. dudm@bit.edu.cn.

Org Biomol Chem ; 17(30): 7182-7191, 2019 08 14.

Article en En | MEDLINE | ID: mdl-31322164

RESUMEN

An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent yields with excellent diastereoselectivities and enantioselectivities (up to 98% yield, >20 : 1 dr and >99% ee). What's more, good yield and high stereoselectivities were obtained in the gram-scale reaction.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article Pais de publicación: Reino Unido

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