Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2...

• Author(s): Pinho e Melo, Teresa M. V. D. ; Cardoso, Ana L. ; Rocha Gonsalves, António M. dA.
• Date: 2003
• Persistent ID: http://hdl.handle.net/10316/5167
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): dehalogenation; 2-halo-2H-azirine-2-carboxylates; chiral 2H-azirine-2-carboxylates
• Document Type: Article
• Language: English

Description

The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobornyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobornyl acetate. http://www.sciencedirect.com/science/article/B6THR-482NK06-7/1/b576da25bb07c16918052295f89735c8