Diastereofacial selectivity in uncatalyzed Diels-Alder cycloadditions involving α,β-unsaturated esters and lactones with stereogenic centers containing oxygen functiionalities

Ramón Casas, Teodor Parella, Vicenç Branchadell, Antonio Oliva, Rosa M. Ortuño, André Guingant

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Resum

Both experimental and theoretical studies on the Diels-Alder cycloadditions of dienophiles 1, 2 and 3 to different dienes show that the observed diastereofacial selectivity results from a combination of electronic and steric interactions. The traditional Felkin-Anh mode is not appropriate for these cases. Several new chiral synthetic building blocks have been prepared. © 1992.
Idioma originalAnglès
Pàgines (de-a)2659-2680
RevistaTetrahedron
Volum48
Número13
DOIs
Estat de la publicacióPublicada - 27 de març 1992

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