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Practical Syntheses of N-Acetyl (E)-β-Arylenamides.
writer:Zhihua Cai, Guodu Liu, Guangjun Jiao, Chris H Senanayake, Wenjun Tang.*
keywords:N-Acetyl (E)-β-Arylenamides
source:期刊
specific source:Synthesis 2013, 45, 3355-3360. (DOI: 10.1055/s-0033-1339976, communication, IF = 2.867, Citation: 3)
Issue time:2013年

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.