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Title: Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
Authors: Pinho e Melo, Teresa M. V. D. 
Cardoso, Ana L. 
Rocha Gonsalves, António M. dA. 
Keywords: dehalogenation; 2-halo-2H-azirine-2-carboxylates; chiral 2H-azirine-2-carboxylates
Issue Date: 2003
Citation: Tetrahedron. 59:13 (2003) 2345-2351
Abstract: 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.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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