Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state
作者:Ayhan S. Demir、Ömer Reis、Ilker Esiringü、Barbaros Reis、Sehriban Baris
DOI:10.1016/j.tet.2006.10.036
日期:2007.1
Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate-phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. (c) 2006 Elsevier Ltd. All rights reserved.