TETRAHEDRON, vol.63, no.1, pp.160-165, 2007 (SCI-Expanded)
Article / Article
Science Citation Index Expanded (SCI-EXPANDED), Scopus
acylphosphonates, cyanohydrin O-phosphates, acyl anion, rearrangements, carboxylic acids, PHOSPHONATE-PHOSPHATE REARRANGEMENT, ENANTIOSELECTIVE SYNTHESIS, CYANO-PHOSPHORYLATION, FACILE SYNTHESIS, ACYLSILANES, CONVENIENT, CATALYST, UMPOLUNG, KETONES
Middle East Technical University Affiliated:
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.