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Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction
Author(s) -
Džambaski Zdravko,
Bondžić Aleksandra M.,
Triandafillidi Ierasia,
Kokotos Christoforos G.,
Bondžić Bojan 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.202100630
Subject(s) - iminium , chemistry , cyclopropanation , enamine , nucleophile , catalysis , ion , organocatalysis , organic chemistry , ring (chemistry) , photochemistry , combinatorial chemistry , enantioselective synthesis
Herein, we demonstrate that organic, single‐electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron‐rich enamines to iminium ions. These iminium ions take part in a subsequent Michael‐initiated ring‐closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one‐pot transformation represents the additional example of saturated aldehydes being used in the coupled one‐pot processes.