Synthesis of 1,3‐Amino Alcohols by Hydroxy‐Directed Aziridination and Aziridine Hydrosilylation |
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| Authors: | Dr. Yong‐Qiang Zhang Fabian Bohle Robin Bleith Dr. Gregor Schnakenburg Prof. Dr. Stefan Grimme Prof. Dr. Andreas Gansäuer |
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| Affiliation: | 1. Kekulé-Institut für Organische Chemie und Biochemie, Universit?t Bonn, Bonn, Germany;2. Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Universit?t Bonn, Bonn, Germany;3. Institut für Anorganische Chemie, Universit?t Bonn, Bonn, Germany |
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| 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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| Keywords: | 1,3-amino alcohols aziridination diastereoselectivity hydrosilylation reaction mechanisms |
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