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Electrochemical Deallylation of α‐Allyl Cyclic Amines and Synthesis of Optically Active Quaternary Cyclic Amino Acids
Author(s) -
Kirira Peter G.,
Kuriyama Masami,
Onomura Osamu
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903512
Subject(s) - electrochemistry , amine gas treating , chemistry , yield (engineering) , cyclic amines , alkyl , optically active , anodic oxidation , alpha (finance) , anode , organic chemistry , medicinal chemistry , electrode , materials science , metallurgy , medicine , construct validity , nursing , patient satisfaction
Electrochemical oxidation of α‐allylated and α‐benzylated N ‐acylated cyclic amines by using a graphite anode easily affords the corresponding α‐methoxylated products with up to 76 % yield. Ease of oxidation was affected by the type of electrode, the size of cyclic amine, and the nature of the protecting group. This method was successfully applied to the synthesis of optically active N ‐acylated α‐alkyl‐α‐amino acid esters with up to 99 % ee .