Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.21/1017
Título: Asymmetric synthesis of N-aryl aziridines
Autor: Aires-de-Sousa, João
Prabhakar, Sundaresan
Lobo, Ana M.
Rosa, Ana M.
Gomes, Mário
Corvo, Marta C.
Williams, David J.
White, Andrew J.
Palavras-chave: Chemistry
Data: 2001
Editora: Pergamon
Citação: Aires-de-Sousa J, Prabhakar S, Lobo AM, Rosa AM, Gomes M, Corvo MC, Williams DJ, White AJ. Asymmetric synthesis of N-aryl aziridines. Tetrahedron Asymmetry. 2001;12:3349-65.
Resumo: The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (−)-8-phenylmenthol, (−)-quinine and (−)-Oppolzer’s sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer’s auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantioselection and a mechanism is proposed for the aziridination reaction.
Peer review: yes
URI: http://hdl.handle.net/10400.21/1017
ISSN: 1362-511X
Versão do Editor: http://www.ingentaconnect.com/content/els/09574166/2002/00000012/00000024/art00548
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