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Organocatalyzed α‐Oxyamination of Aldehydes Using Anodic Oxidation
Author(s) -
Bui NhatNguyen,
Ho XuanHuong,
Mho Sunil,
Jang HyeYoung
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900871
Subject(s) - chemistry , enamine , electrochemistry , cyclic voltammetry , amine gas treating , yield (engineering) , cationic polymerization , aldehyde , catalysis , electrolyte , anode , organic chemistry , organocatalysis , electrosynthesis , cyclic amines , supporting electrolyte , coupling reaction , inorganic chemistry , enantioselective synthesis , electrode , materials science , metallurgy
Electrochemical oxidation was performed during the organocatalyzed α‐oxyamination of aldehydes by using a one‐compartment electrolytic cell under galvanostatic conditions. In the presence of substoichiometric amounts of sec ‐amines, the desired coupling products were formed in good yield. The asymmetric variant of the α‐oxyamination of aldehydes was examined by using chiral sec ‐amines. Control experiments and cyclic voltammetry confirmed the key intermediate of this reaction to be the cationic radical of the enamine derived from the sec ‐amine catalysts and aldehydes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)