Synthesis of β-chloro-α-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates

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 β-chloro-α-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.

GRAPHICAL ABSTRACT

Keywords:

• Aziridine-2-phosphonates
• regioselective ring opening
• β-chloro-α-aminophosphonates

Acknowledgments

We thank the Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. 114Z161) and Middle East Technical University (METU) for the financial support.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

We thank the Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. 114Z161) and Middle East Technical University (METU) for the financial support.