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Highly enantioselective introduction of bis(alkoxycarbonyl)methyl group into the 2-position of piperidine skeleton


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Title: Highly enantioselective introduction of bis(alkoxycarbonyl)methyl group into the 2-position of piperidine skeleton
Authors: Matsumura, Yoshihiro / Minato, Daishiro / Onomura, Osamu
Issue Date: 1-Jan-2007
Publisher: Elsevier
Citation: Journal of Organometallic Chemistry 692(1-3) pp.654-663, 2007
Abstract: Copper ion catalyzed carbon?carbon bond forming reaction of N-acyliminium ions with diaryl malonates was achieved with high enantioselectivity. The key intermediates in the method were 2-methoxy-3,4-didehydropiperidines, which were easily prepared through electrochemical oxidation of 1-(p-methoxybenzoyl)piperidine in methanol followed by the conversion of the oxidation product to didehydropiperidine derivative, which was subjected to a chiral Cu(II) catalyzed coupling reaction with diaryl malonates affording diaryl 2-piperidylmalonates. The maximum % ee (ee, enantiomeric excess) was 97% when di-p-chlorophenyl malonate was used as a nucleophile.
Keywords: Optically active 2-alkylpiperidines / 2-Methoxy-3,4-didehydropiperidines / Electrochemical oxidation / Catalytic asymmetric reaction / Copper ion-catalyzed
URI: http://hdl.handle.net/10069/16338
ISSN: 0022328X
DOI: 10.1016/j.jorganchem.2006.04.039
Rights: Copyright © 2007 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/16338

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