1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones

1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones

Autor Dias, Luiz C. Google Scholar
Aguilar, Andrea M. Autor UNIFESP Google Scholar
Instituição Universidade Estadual de Campinas (UNICAMP)
Universidade Federal de São Paulo (UNIFESP)
Resumo This tutorial review describes that high levels of substrate-controlled, 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of beta-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate pi-facial selectivity critically dependent upon the nature of the beta-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products with remarkable pharmacological activities. At present, the origin of the high level of 1,5-anti induction obtained with the boron enolates is unclear, although a model based on hydrogen bonding between the beta-alkoxy oxygen and the formyl aldehyde hydrogen has recently been proposed.
Idioma Inglês
Data de publicação 2008-01-01
Publicado em Chemical Society Reviews. Cambridge: Royal Soc Chemistry, v. 37, n. 3, p. 451-469, 2008.
ISSN 0306-0012 (Sherpa/Romeo, fator de impacto)
Publicador Royal Soc Chemistry
Extensão 451-469
Fonte http://dx.doi.org/10.1039/b701081h
Direito de acesso Acesso restrito
Tipo Resenha
Web of Science WOS:000252757500002
Endereço permanente http://repositorio.unifesp.br/handle/11600/30304

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