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High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines

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Title: High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines
Authors: Libendi, Samuel S. / Demizu, Yosuke / Matsumura, Yoshihiro / Onomura, Osamu
Issue Date: Apr-2008
Publisher: Elsevier
Citation: Tetrahedron, 64(18), pp.3935-3942; 2008
Abstract: N-Protecting groups of α-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into α′-methoxylated compounds, while N-cyano derivatives changed into α-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the α-methoxylated compounds protected with cyano group afforded α,α-disubstituted cyclic amines.
Keywords: Cyclic amines / Electrochemical oxidation / Regioselective
URI: http://hdl.handle.net/10069/16314
ISSN: 00404020
DOI: doi:10.1016/j.tet.2008.02.060
Rights: Copyright © 2008 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/16314

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