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

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dc.contributor.author Dias, Luiz C.
dc.contributor.author Aguilar, Andrea M. [UNIFESP]
dc.date.accessioned 2016-01-24T13:49:24Z
dc.date.available 2016-01-24T13:49:24Z
dc.date.issued 2008-01-01
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.issn 0306-0012
dc.identifier.uri http://repositorio.unifesp.br/handle/11600/30304
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.format.extent 451-469
dc.language.iso eng
dc.publisher Royal Soc Chemistry
dc.relation.ispartof Chemical Society Reviews
dc.rights Acesso restrito
dc.title 1,5-asymmetric induction in boron-mediated aldol reactions of beta-oxygenated methyl ketones en
dc.type Resenha
dc.contributor.institution Universidade Estadual de Campinas (UNICAMP)
dc.contributor.institution Universidade Federal de São Paulo (UNIFESP)
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.identifier.doi 10.1039/b701081h
dc.description.source Web of Science
dc.identifier.wos WOS:000252757500002



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