Darzens Reaction of Acyl Phosphonates with alpha-Bromo Ketones: Selective Synthesis of cis- and trans-Epoxyphosphonates

DEMİR A. G., Emrullahoglu M., Pirkin E., Akca N.

JOURNAL OF ORGANIC CHEMISTRY, cilt.73, sa.22, ss.8992-8997, 2008 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 22
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1021/jo801818p
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8992-8997
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Acyl phosphonates with alpha-halo ketones in the presence of bases at room temperature afford cis- and trans-epoxyphosphonates in good chemical yields and high selectivities using different bases. The diastereoselectivity of this reaction is easily controlled by changing the base. Changing the base from CS(2)CO(3) to DBU changed the diastereomeric ratio (trans/cis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete conversion to the corresponding cis isomer.