Diastereoselective trimolecular condensation between indole, Meldrum's acid and chiral sugar-derived aldehydes
Fiche publication
Date publication
février 2010
Auteurs
Membres identifiés du Cancéropôle Est :
Pr SAPI Janos, Dr GERARD Stéphane
Tous les auteurs :
Dardennes E, Gerard S, Petermann C, Sapi J
Lien Pubmed
Résumé
The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate. (C) 2010 Elsevier Ltd. All rights reserved.
Référence
Tetrahedron-asymmetry. 2010 Feb 22;21(2):208-15