Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state

Demir A. S., Reis O., Esiringu I., Reis B., Baris S.

TETRAHEDRON, cilt.63, sa.1, ss.160-165, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 1
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2006.10.036
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.160-165
  • Anahtar Kelimeler: acylphosphonates, cyanohydrin O-phosphates, acyl anion, rearrangements, carboxylic acids, PHOSPHONATE-PHOSPHATE REARRANGEMENT, ENANTIOSELECTIVE SYNTHESIS, CYANO-PHOSPHORYLATION, FACILE SYNTHESIS, ACYLSILANES, CONVENIENT, CATALYST, UMPOLUNG, KETONES
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.