Zhang Yong-Qiang, Bohle Fabian, Bleith Robin, Schnakenburg Gregor, Grimme Stefan, Gansäuer Andreas
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Universität Bonn, Beringstrasse 4, 53115, Bonn, Germany.
Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13528-13532. doi: 10.1002/anie.201808034. Epub 2018 Sep 19.
We describe an approach to N-tosyl 1,3-amino alcohols that consists of a diastereoselective aziridination reaction of acyclic allylic alcohols and an unprecedented regioselective hydrosilylation of α-hydroxy aziridines. The products contain up to three contiguous stereocenters. Computational studies outline key aspects of the aziridination mechanism, which is different and more intricate than anticipated.
我们描述了一种合成N-对甲苯磺酰基-1,3-氨基醇的方法，该方法包括无环烯丙醇的非对映选择性氮杂环丙烷化反应以及α-羟基氮杂环丙烷前所未有的区域选择性硅氢化反应。产物含有多达三个相邻的立体中心。计算研究概述了氮杂环丙烷化反应机理的关键方面，该机理与预期不同且更为复杂。
