Synthesis of Functionalized Novel alpha-Amino-beta-alkoxyphosphonates through Regioselective Ring Opening of Aziridine-2-phosphonates


POLAT ÇAKIR S., Beksultanova N., DOĞAN Ö.

HELVETICA CHIMICA ACTA, vol.102, no.11, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 102 Issue: 11
  • Publication Date: 2019
  • Doi Number: 10.1002/hlca.201900199
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Çanakkale Onsekiz Mart University Affiliated: Yes

Abstract

Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions provided functionalized alpha-amino-beta-alkoxyphosphonates in 40-91 % yield.