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Chemo‐ and Diastereoselectivities in the Electrochemical Reduction of Maleimides
Author(s) -
Rix Kathryn,
Kelsall Geoffrey H.,
Hellgardt Klaus,
Hii King Kuok Mimi
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201403184
Subject(s) - chemistry , succinimides , electrochemistry , substituent , tautomer , alkene , alkyne , stereoselectivity , catalysis , diastereomer , photochemistry , enol , combinatorial chemistry , electrode , organic chemistry
The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4‐dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid‐catalyzed tautomerization of a half‐enol occurring through a double hydrogen‐transfer mechanism.