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酰胺辅助的环丙烷开环分子内[3+2]环化反应:一种简便且非对映选择性地构建(±)-山椒素三环核心结构的方法。

Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine.

作者信息

Xiao Jun-An, Xia Peng-Ju, Zhang Xing-Yu, Chen Xiao-Qing, Ou Guang-Chuan, Yang Hua

机构信息

College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.

Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South/Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P. R. China.

出版信息

Chem Commun (Camb). 2016 Feb 4;52(10):2177-80. doi: 10.1039/c5cc07485a.

DOI:10.1039/c5cc07485a
PMID:26727144
Abstract

The highly diastereoselective intramolecular [3+2] annulation via the ring-opening of a cyclopropane diester derivative has been developed to construct a dihydroquinolinone scaffold. A series of tricyclic dihydroquinolinones bearing one or two all-carbon quaternary stereogenic centers were obtained in good yields and excellent diastereoselectivities (up to 20 : 1 dr). Moreover, the amide-linking mode shows obviously beneficial effects on the ring-opening of cyclopropane.

摘要

通过环丙烷二酯衍生物的开环反应,开发了一种高度非对映选择性的分子内[3+2]环化反应,用于构建二氢喹啉酮骨架。一系列带有一个或两个全碳季立体中心的三环二氢喹啉酮以良好的产率和优异的非对映选择性(高达20:1的dr值)得到。此外,酰胺连接模式对环丙烷的开环反应显示出明显的有利影响。

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