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Synthesis of 1,3‐Amino Alcohols by Hydroxy‐Directed Aziridination and Aziridine Hydrosilylation
Author(s) -
Zhang YongQiang,
Bohle Fabian,
Bleith Robin,
Schnakenburg Gregor,
Grimme Stefan,
Gansäuer Andreas
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808034
Subject(s) - aziridine , hydrosilylation , regioselectivity , stereocenter , chemistry , allylic rearrangement , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , ring (chemistry)
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.