Artículos de revistas
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]
Registro en:
Quimica Nova. , v. 30, n. 8, p. 2007 - 2015, 2007.
1004042
2-s2.0-38949149334
Autor
Dias L.C.
Aguilar A.M.
Institución
Resumen
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. 30 8 2007 2015 Cowden, C.J., Paterson, I., (1997) Org. React, 51, p. 1 Schetter, B., Mahrwald, R., (2006) Angew. Chem., Int. Ed, 45, p. 7506 Franklin, A.S., Paterson, I., (1994) Contemp. Org. Synth, 1, p. 317 Paterson, I.E., (1991) Comprehensive Organic Synthesis, 2, p. 301. , Heathcock, C. 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