B A Hopkins1, J P Wolfe1. 1. University of Michigan, Department of Chemistry, 930 N. University Ave., Ann Arbor, MI 48109-1055, USA.
Abstract
A catalyst composed of Pd2(dba)3 and (S)-Siphos-PE provides excellent results in Pd-catalyzed alkene carboamination reactions between aniline derivatives bearing pendant alkenes and aryl or alkenyl halides. These transformations generate tetrahydroquinolines and tetrahydroquinoxalines that contain quaternary carbon stereocenters with high levels of asymmetric induction. In addition this catalyst also effects the asymmetric synthesis of tetrahydroisoquinolines via related transformations of 2-allylbenzylamines. In contrast to most other approaches to the asymmetric synthesis of these compounds, which frequently involve functional group interconversion or a single C-C or C-N bond-forming event, the carboamination reactions generate both a C-N bond, a C-C bond, and a stereocenter.
A catalyst composed of n class="Chemical">pan class="Chemical">Pd2(dba)3 anclass="Chemical">pan>d n class="Chemical">(S)-Siphos-PE provides excellent results in n class="Chemical">Pd-catalyzed alkene carboamination reactions between aniline derivatives bearing pendant alkenes and aryl or alkenyl halides. These transformations generate tetrahydroquinolines and tetrahydroquinoxalines that contain quaternary carbon stereocenters with high levels of asymmetric induction. In addition this catalyst also effects the asymmetric synthesis of tetrahydroisoquinolines via related transformations of 2-allylbenzylamines. In contrast to most other approaches to the asymmetric synthesis of these compounds, which frequently involve functional group interconversion or a single C-C or C-N bond-forming event, the carboamination reactions generate both a C-N bond, a C-C bond, and a stereocenter.
Authors: Nicholas J Race; Adele Faulkner; Gabriele Fumagalli; Takayuki Yamauchi; James S Scott; Marie Rydén-Landergren; Hazel A Sparkes; John F Bower Journal: Chem Sci Date: 2016-11-24 Impact factor: 9.825