Vila Carlos, Rostoll-Berenguer Jaume, Sánchez-García Rubén, Blay Gonzalo, Fernández Isabel, Muñoz M Carmen, Pedro José R
Departament de Química Orgànica, Facultat de Química , Universitat de València , Dr. Moliner 50 , Burjassot, València 46100 , Spain.
Departament de Física Aplicada , Universitat Politècnica de València , Camino de Vera s/n , València 46022 , Spain.
J Org Chem. 2018 Jun 15;83(12):6397-6407. doi: 10.1021/acs.joc.8b00612. Epub 2018 Jun 7.
An asymmetric catalytic reaction of hydroxyindoles with nitroalkenes leading to the Friedel-Crafts alkylation in the carbocyclic ring of indole is presented. The method is based on the activating/directing effects of the hydroxy group situated in the carbocyclic ring of the indole providing nitroalkylated indoles functionalizated at the C-4, C-5, and C-7 positions with high yield, regio-, and enantioselectivity. The optically enriched nitroalkanes were transformed efficiently in optically enriched 2-amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole.
本文介绍了一种羟基吲哚与硝基烯烃的不对称催化反应，该反应可实现吲哚碳环上的傅克烷基化。该方法基于吲哚碳环上羟基的活化/导向作用，能以高收率、区域选择性和对映选择性得到在C-4、C-5和C-7位官能化的硝基烷基化吲哚。光学富集的硝基烷烃能有效地转化为带有碳环取代吲哚的光学富集的2-氨基-1,1-二芳基烷烃。
