National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry , Chinese Academy of Sciences , Chengdu 610041 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
J Org Chem. 2019 Apr 5;84(7):4381-4391. doi: 10.1021/acs.joc.9b00401. Epub 2019 Mar 25.
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.
已开发出一种通过 2-硝基苯并呋喃和 2-硝基苯并噻吩与 2-氨基查耳酮的有机催化去芳构化的氮杂迈克尔加成/迈克尔加成级联反应，为获得一系列具有三个连续立体中心的光学活性四氢苯并呋喃[3,2-b]喹啉和四氢苯并[4,5]噻吩[3,2-b]喹啉开辟了新途径，具有优异的非对映选择性和对映选择性（所有情况 dr>20:1，ee 值高达 99%）。该研究以氮杂迈克尔加成反应为起点，首次实现了 2-硝基苯并呋喃和 2-硝基苯并噻吩的不对称去芳构化级联反应。该方法的潜在应用通过制备规模实验和产物的多功能转化得到了证明。
