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通过有机催化的1,3-偶极环加成反应实现含CF3的螺[吡咯烷-3,2'-吲哚酮]的不对称合成。

The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2'-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction.

作者信息

Ma Mingxia, Zhu Yuanyuan, Sun Quantao, Li Xiaoyuan, Su Jinhuan, Zhao Long, Zhao Yanyan, Qiu Shuai, Yan Wenjin, Wang Kairong, Wang Rui

机构信息

Department of Pharmacology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China.

出版信息

Chem Commun (Camb). 2015 May 25;51(42):8789-92. doi: 10.1039/c4cc10216a.

DOI:10.1039/c4cc10216a
PMID:25915470
Abstract

A new strategy for the construction of optically active 5'-CF3 spiro[pyrrolidin-3,2'-oxindole] was described. A series of unprecedented 1,3-dipoles were obtained by condensation of CF3CH2NH2 with isatins. The 1,3-dipolar cycloaddition reactions of these ketimines with enals gave the products bearing four contiguous stereogenic centers in excellent yields, diastereoselectivities and enantioselectivities.

摘要

描述了一种构建光学活性5'-CF3螺环[吡咯烷-3,2'-吲哚酮]的新策略。通过CF3CH2NH2与异吲哚酮的缩合反应得到了一系列前所未有的1,3-偶极体。这些酮亚胺与烯醛的1,3-偶极环加成反应以优异的产率、非对映选择性和对映选择性得到了带有四个相邻手性中心的产物。

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