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Journal of the Brazilian Chemical Society

On-line version ISSN 1678-4790

Abstract

ANDRADE, Carlos Kleber Z.; ROCHA, Rafael O.; RUSSOWSKY, Dennis  and  GODOY, Marla N.. Studies on the niobium pentachloride-mediated nucleophilic additions to an enantiopure cyclic N-acyliminium ion derived from (S)-malic acid. J. Braz. Chem. Soc. [online]. 2005, vol.16, n.3b, pp. 535-539. ISSN 1678-4790.  http://dx.doi.org/10.1590/S0103-50532005000400007.

A adição nucleofílica de vários nucleófilos (alilsilano, silil enol éter da acetofenona, indol e N-sulfonilindol) ao íon N-acilimínio enantiopuro 1a, derivado do ácido (S)-málico, promovida por pentacloreto de nióbio é descrita. Os produtos foram obtidos em bons rendimentos e em diastereosseletividades variáveis dependendo do volume estérico do nucleófilo. Os melhores resultados foram obtidos com a adição de indóis.

Keywords : N-acyliminium ions; niobium pentachloride; nucleophilic additions; diastereoselectivity.

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