Reaction of 2 H-Azirine Phosphine Oxide and-Phosphonates with Nucleophiles. Stereoselective Synthesis of Functionalized Aziridines and α-and β- …

F Palacios, AM Ochoa de Retana…

Index: Palacios, Francisco; Ochoa De Retana, Ana M.; Alonso, Jose M. Journal of Organic Chemistry, 2005 , vol. 70, # 22 p. 8895 - 8901

Full Text: HTML

Citation Number: 37

Abstract

A simple and efficient stereoselective synthesis of aziridine-2-phosphonate 3, and- phosphine oxide 5 by diastereoselective addition of Grignard reagents to 2 H-azirine phosphonate 1 and-phosphine oxide 4 is reported. Similarly, the addition of heterocyclic amines and benzenethiol to aziridines 1 and 4 yielded functionalized aziridines 10, 11, and 18. These aziridines are used as intermediates for the regioselective synthesis of β- ...