Catalytic asymmetric synthesis of N -substituted tetrahydroquinoxalines via regioselective Heyns rearrangement and stereoselective transfer hydrogenation in one pot.

Autor: Huang J; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn.; University of Chinese Academy of Sciences China., Li GX; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn., Yang GF; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn., Fu DQ; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn., Nie XK; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn., Cui X; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn., Zhao JZ; College of Art and Sciences, Shanxi Agricultural University Taigu Shanxi 030800 China., Tang Z; Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science Chengdu Sichuan 610041 China ligx@cib.ac.cn tangzhuo@cib.ac.cn.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2021 Feb 19; Vol. 12 (13), pp. 4789-4793. Date of Electronic Publication: 2021 Feb 19.
DOI: 10.1039/d0sc06264b
Abstrakt: N -Substituted tetrahydroquinoxalines (37 examples) were step-economically obtained in good yield (<97%) and ee (<99%) with readily available substrates. The reaction proceeds through an interesting regioselective Heyns rearrangement/enantioselective transfer hydrogenation in one pot. The substrate scope and the reaction mechanism were systematically investigated.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE