Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/106563
Type: Artigo de periódico
Title: 1,5-asymmetric Induction In Boron-mediated Aldol Reactions Of β-oxygenated Methyl Ketones
Author: Dias L.C.
Aguilar A.M.
Abstract: This tutorial review describes that high levels of substrate-controlled, 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of β-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate π-facial selectivity critically dependent upon the nature of the β-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 β-alkoxy oxygen and the formyl aldehyde hydrogen has recently been proposed. © The Royal Society of Chemistry 2008.
Editor: 
Rights: aberto
Identifier DOI: 10.1039/b701081h
Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-38549167376&partnerID=40&md5=9d4ae2c9e2fd41e2e88397fdda18bc20
Date Issue: 2008
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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