Author |
Dias, Luiz C.
![]() Aguilar, Andrea M. ![]() ![]() |
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 |
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Access rights | Closed access |
Type | Review |
Web of Science ID | WOS:000252757500002 |
URI | http://repositorio.unifesp.br/handle/11600/30304 |
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