Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/104430
Type: Artigo de periódico
Title: 1,5-asymmetric Induction In The Boron-mediated Aldol Reactions Of β-oxygenated Methyl Ketones [indução Assimétrica 1,5-anti Na Adição De Enolatos De Boro De Metilcetonas β-oxigenadas A Aldeídos]
Author: Dias L.C.
Aguilar A.M.
Abstract: High levels of substrate-based 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. 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 a hydrogen bonding between the alkoxy oxygen and the formyl hydrogen has been recently proposed.
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Rights: aberto
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Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-38949149334&partnerID=40&md5=bf5680b0060ab07f08d3af976e3b91ee
Date Issue: 2007
Appears in Collections:Unicamp - Artigos e Outros Documentos

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