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

Angewandte Chemie
Yong-Qiang ZhangAndreas Gansäuer

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.

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