Premium
Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza‐Darzens Reactions
Author(s) -
Trost Barry M.,
Saget Tanguy,
Hung ChaoI Joey
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201607845
Subject(s) - enantioselective synthesis , stereocenter , chemistry , catalysis , nucleophile , combinatorial chemistry , derivatization , organic chemistry , organocatalysis , high performance liquid chromatography
Herein, we report a Zn‐ProPhenol catalyzed aza‐Darzens reaction using chlorinated aromatic ketones as nucleophilic partners for the efficient and enantioselective construction of complex trisubstituted aziridines. The α‐chloro‐β‐aminoketone intermediates featuring a chlorinated tetrasubstituted stereocenter can be isolated in high yields and selectivities for further derivatization. Alternatively, they can be directly transformed to the corresponding aziridines in a one‐pot fashion. Of note, the reaction can be run on gram‐scale with low catalyst loading without impacting its efficiency. Moreover, this methodology was extended to α‐bromoketones which are scarcely used in enantioselective catalysis because of their sensitivity and lack of accessibility.