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, vol.193, no.12, pp.858-864, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 193 Issue: 12
  • Publication Date: 2018
  • Doi Number: 10.1080/10426507.2018.1513521
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.858-864
  • Keywords: Aziridine-2-phosphonates, regioselective ring opening, beta-chloro-alpha-aminophosphonates, ASYMMETRIC-SYNTHESIS, AZIRIDINE 2-PHOSPHONATES, STEREOSELECTIVE-SYNTHESIS, PHOSPHONATES, KETOPHOSPHONATES, REACTIVITY, REDUCTION, ACIDS
  • Middle East Technical University Affiliated: Yes

Abstract

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.