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Synthesis 2013; 45(24): 3355-3360
DOI: 10.1055/s-0033-1339976
DOI: 10.1055/s-0033-1339976
paper
Practical Syntheses of N-Acetyl (E)-β-Arylenamides
Further Information
Publication History
Received: 20 August 2013
Accepted after revision: 21 September 2013
Publication Date:
14 October 2013 (online)
Abstract
A facile and practical method for the preparation of (E)-β-arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key chiral intermediate of tamsulosin by asymmetric hydrogenation.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For selected reviews of transition-metal-catalyzed asymmetric hydrogenation, see: