Organocatalyzed Asymmetric Dearomative Aza-Michael/Michael Addition Cascade of 2-Nitrobenzofurans and 2-Nitrobenzothiophenes with 2-Aminochalcones
Organocatalyzed Asymmetric Dearomative Aza-Michael/Michael Addition Cascade of 2-Nitrobenzofurans and 2-Nitrobenzothiophenes with 2-Aminochalcones
复制标题
2-硝基苯并呋喃和 2-硝基苯并噻吩与 2-氨基查尔酮的有机催化不对称脱芳香剂 Aza-Michael/Michael 加成级联
DOI：
10.1021/acs.joc.9b00401
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发表时间：
2019
影响因子：
3.6
通讯作者：
Yuan Wei-Cheng
中科院分区：
文献类型：
--
作者：
Zhou Xiao-Jian;Zhao Jian-Qiang;Chen Xin-Meng;Zhuo Jun-Rui;Zhang Yan-Ping;Chen Yong-Zheng;Zhang Xiao-Mei;Xu Xiao-Ying;Yuan Wei-Cheng
本文报道了2-硝基苯并呋喃和2-硝基苯并噻吩与2-氨基查尔酮的有机催化脱芳氮Michael/Michael加成级联反应，为获得一系列具有三个相邻立体中心的光学活性四氢苯并呋喃并[3，2-B]喹啉和四氢苯并[4，5]噻吩并[3，2-B]喹啉开辟了一条新的途径。本研究首次报道了2-硝基苯并呋喃和2-硝基苯并噻吩的不对称脱芳级联反应。该方法的潜在应用已通过放大实验和产物的多方面转化得到证实。
An organocatalyzed dearomative aza-Michael/Michael addition cascade of 2-nitrobenzofurans and 2-nitrobenzothiophenes with 2-aminochalcones has been developed, opening a new channel to access a series of optically active tetrahydrobenzofuro[3,2-b]quinolines and tetrahydrobenzo[4,5]thieno[3,2-b]quinolines bearing three contiguous stereocenters with excellent diastereo- and enantioselectivities (all cases >20:1 dr, up to 99% ee). This study features the first asymmetric dearomative cascade reaction of 2-nitrobenzofurans and 2-nitrobenzothiophenes beginning with aza-Michael addition. The potential applications of the methodology were demonstrated by the preparative-scale experiment and the versatile transformations of the products.