Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

• Tipo: Artigo em Revista Científica Internacional
• Data: 2013

Autores

Xerardo Garcia Mera (Autor) Outra; Maria J Alves (Autor) Outra; Albertino Goth (Autor) Outra; Maria Luisa do Vale (Autor) FCUP; Jose E Rodriguez Borges (Autor) FCUP

Revista

Título: Tetrahedron

Vol. 69

Páginas: 2909-2919

ISSN: 0040-4020

Editora: Elsevier

Indexação

ISI Web of Knowledge - 8 Citações

Scopus - 8 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

CORDIS: Ciências Físicas > Química > Química orgânica

Outras Informações

ID Authenticus: P-005-1MZ

DOI: 10.1016/j.tet.2013.02.027

Abstract (EN): Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11