Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 24, Pages 3355-3360Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1339976
Keywords
beta-arylenamides; iron(II) acetate; reductive acylation; beta-arylamines; tamsulosin
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Funding
- 'Thousand Plan' Youth program
- Innovation Fund of State Key Laboratory of Bioorganic and Natural Products Chemistry
- [NSFC-21272254]
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A facile and practical method for the preparation of (E)--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.
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