Stereoconvergent, Redox-Neutral Access to Tetrahydroquinoxalines through Relay Epoxide Opening/Amination of Alcohols.
Guangda XuGuoqiang YangYue WangPan-Lin ShaoJia Ning Nicolette YauBing LiuYunbo ZhaoYe SunXinxin XieShuo WangYao ZhangLixin XiaYu ZhaoPublished in: Angewandte Chemie (International ed. in English) (2019)
We present an economical catalytic procedure to convert readily available 1,2-diaminobenzenes and terminal epoxides into valuable 1,2,3,4-tetrahydroquinoxalines in a highly enantioselective fashion. This procedure operates through relay zinc and iridium catalysis, and achieves redox-neutral and stereoconvergent production of valuable chiral heterocycles from racemic starting materials with water as the only side product. The use of commercially available reagents and catalysts and a convenient procedure also make this catalytic method attractive for practical application.