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

Author Dias, Luiz C. Google Scholar
Aguilar, Andrea M. Autor UNIFESP Google Scholar
Institution Universidade Estadual de Campinas (UNICAMP)
Universidade Federal de São Paulo (UNIFESP)
Abstract 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.
Language English
Date 2008-01-01
Published in Chemical Society Reviews. Cambridge: Royal Soc Chemistry, v. 37, n. 3, p. 451-469, 2008.
ISSN 0306-0012 (Sherpa/Romeo, impact factor)
Publisher Royal Soc Chemistry
Extent 451-469
Origin http://dx.doi.org/10.1039/b701081h
Access rights Closed access
Type Review
Web of Science ID WOS:000252757500002
URI http://repositorio.unifesp.br/handle/11600/30304

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