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Manganese Catalyzed Enantioselective Epoxidation of α , β ‐Unsaturated Amides with H 2 O 2
Author(s) -
Ottenbacher Roman V.,
Kurganskiy Vladimir I.,
Talsi Evgenii P.,
Bryliakov Konstantin P.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100198
Subject(s) - chemistry , enantioselective synthesis , manganese , moiety , catalysis , substrate (aquarium) , pyridine , yield (engineering) , medicinal chemistry , stereochemistry , organic chemistry , oceanography , materials science , metallurgy , geology
Abstract Herewith, we report the enantioselective epoxidation of electron‐deficient cis ‐ and trans‐α , β ‐unsaturated amides with the environmentally benign oxidant H 2 O 2 . The catalysts ‐ manganese complexes with bis ‐amino‐ bis ‐pyridine and structurally related ligands ‐ exhibit reasonably high efficiency (up to 100 TON) and excellent chemo‐ and enantioselectivity (up to 100% and 99% ee , respectively). Crucially, the cis ‐enamides epoxidation enantioselectivity and yield are dramatically enhanced by the presence of NH‐moiety, which effect can be explained by the hydrogen bonding interaction between the cis ‐enamide substrate and the manganese based oxygen transferring species.