1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones
| dc.contributor.author | Dias, Luiz C. | |
| dc.contributor.author | Aguilar, Andrea M. [UNIFESP] | |
| dc.contributor.institution | Universidade Estadual de Campinas (UNICAMP) | |
| dc.contributor.institution | Universidade Federal de São Paulo (UNIFESP) | |
| dc.date.accessioned | 2016-01-24T13:49:24Z | |
| dc.date.available | 2016-01-24T13:49:24Z | |
| dc.date.issued | 2008-01-01 | |
| dc.description.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. | en |
| dc.description.affiliation | Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil | |
| dc.description.affiliation | Universidade Federal de São Paulo, Dept Ciencias Exatas & Terra, BR-09972270 Diadema, SP, Brazil | |
| dc.description.affiliationUnifesp | Universidade Federal de São Paulo, Dept Ciencias Exatas & Terra, BR-09972270 Diadema, SP, Brazil | |
| dc.description.source | Web of Science | |
| dc.format.extent | 451-469 | |
| dc.identifier | http://dx.doi.org/10.1039/b701081h | |
| dc.identifier.citation | Chemical Society Reviews. Cambridge: Royal Soc Chemistry, v. 37, n. 3, p. 451-469, 2008. | |
| dc.identifier.doi | 10.1039/b701081h | |
| dc.identifier.issn | 0306-0012 | |
| dc.identifier.uri | http://repositorio.unifesp.br/handle/11600/30304 | |
| dc.identifier.wos | WOS:000252757500002 | |
| dc.language.iso | eng | |
| dc.publisher | Royal Soc Chemistry | |
| dc.relation.ispartof | Chemical Society Reviews | |
| dc.rights | info:eu-repo/semantics/restrictedAccess | |
| dc.title | 1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones | en |
| dc.type | info:eu-repo/semantics/article |