Selective Synthesis of Substituted Pyrrole-2-phosphine Oxides and -phosphonates from 2H-Azirines and Enolates from Acetyl Acetates and Malonates
- Autoría:
- Francisco Palacios, Ana M. Ochoa de Retana, Ander Velez del Burgo
- Año:
- 2011
- Revista:
- The Journal of Organic Chemistry
- Volumen:
- 76
- Página de inicio - Página de fin:
- 9472 - 9477
- Descripción:
-
A simple and efficient selective synthesis of 1H-pyrrole-2-phosphine oxides 3 and -phosphonates 7 by addition of enolates derived from acetyl acetates to 2H-azirinylphosphine oxide 1 and -phosphonate 6 is reported. Nucleophilic addition of enolates derived from diethyl malonate to 2H-azirines 1 and 6 led to the formation of functionalized 2-hydroxy-1H-pyrrole-5-phosphine oxide 9 and -phosphonate 10, while vinylogous α-aminoalkylphosphine oxides 14 and -phosphonate 15 may be obtained from azirines and the enolate derived from diethyl 2-phenylmalonate. Ring closure of vinylogous derivatives 14 and 15 in the presence of base led to the formation of 1,5-dihydro-3-pyrrolin-2-ones containing a phosphine oxide 17 or a phosphonate group 18.