Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates

Polat-Cakir S., BEKSULTANOVA N., DOĞAN Ö.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.193, sa.12, ss.858-864, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 193 Sayı: 12
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1080/10426507.2018.1513521
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.858-864
  • Anahtar Kelimeler: Aziridine-2-phosphonates, regioselective ring opening, beta-chloro-alpha-aminophosphonates, ASYMMETRIC-SYNTHESIS, AZIRIDINE 2-PHOSPHONATES, STEREOSELECTIVE-SYNTHESIS, PHOSPHONATES, KETOPHOSPHONATES, REACTIVITY, REDUCTION, ACIDS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.