Synthesis of 1,3-Amino Alcohols by Hydroxy-Directed Aziridination and Aziridine Hydrosilylation

Yong-Qiang Zhang; Fabian Bohle; Robin Bleith; Gregor Schnakenburg; Stefan Grimme; Andreas Gansäuer

doi:10.1002/anie.201808034

Synthesis of 1,3-Amino Alcohols by Hydroxy-Directed Aziridination and Aziridine Hydrosilylation

Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13528-13532. doi: 10.1002/anie.201808034. Epub 2018 Sep 19.

Authors

Yong-Qiang Zhang¹, Fabian Bohle², Robin Bleith¹, Gregor Schnakenburg³, Stefan Grimme², Andreas Gansäuer¹

Affiliations

¹ Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
² Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Universität Bonn, Beringstrasse 4, 53115, Bonn, Germany.
³ Institut für Anorganische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.

PMID: 30144271
DOI: 10.1002/anie.201808034

Abstract

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.

Keywords: 1,3-amino alcohols; aziridination; diastereoselectivity; hydrosilylation; reaction mechanisms.

Publication types

Research Support, Non-U.S. Gov't