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5-6-5氮杂三环支架的立体选择性构建:催化不对称氮杂-Piancatelli/狄尔斯-阿尔德反应

Stereoselective construction of 5-6-5 aza-tricyclic scaffolds catalytic asymmetric aza-Piancatelli/Diels-Alder reactions.

作者信息

Wang Lishu, Wang Han, Nie Xukun, Li Jun, Tang Yurong, Cai Yunfei

机构信息

School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 YingbinRoad, 321004 Jinhua, China.

出版信息

Chem Commun (Camb). 2025 Jun 3;61(46):8395-8398. doi: 10.1039/d5cc01888a.

Abstract

A chiral Brønsted acid-catalyzed asymmetric cascade aza-Piancatelli rearrangement/intramolecular Diels-Alder reaction has been developed. This method enables the atom- and step-efficient synthesis of chiral aza-[5,6,5]-tricyclic derivatives with multiple contiguous stereocenters in a highly enantioselective manner from readily available -pentadienylanilines and 2-furylcarbinols.

摘要

已开发出一种手性布朗斯特酸催化的不对称串联氮杂-Piancatelli重排/分子内狄尔斯-阿尔德反应。该方法能够以高度对映选择性的方式,从易得的戊二烯基苯胺和2-呋喃甲醇高效地原子经济性和步骤经济性地合成具有多个相邻立体中心的手性氮杂-[5,6,5]-三环衍生物。

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