Origin of chiral induction in radical reactions with the diastereoisomers (5R)- and (5S)-5-l-menthyloxyfuran-2[5H]-one.
Fiche publication
Date publication
mars 2004
Auteurs
Membres identifiés du Cancéropôle Est :
Dr NUZILLARD Jean-Marc
Tous les auteurs :
Marinkovic S, Brule C, Hoffmann N, Prost E, Nuzillard JM, Bulach V
Lien Pubmed
Résumé
Acetalization of 5-hydroxyfuran-2[5H]-one with l-menthol yields (5R)- (1) and (5S)-5-l-menthyloxyfuran-2[5H]-one (2) in equal amounts. The diastereomer 1 crystallizes preferentially. For the first time, the isolation of pure diastereoisomer 2 is reported. Different diastereoselectivities were observed in the radical tandem reaction of 1 and 2 with N,N-dimethylaniline. The privileged conformations in solution of the substrates and the products of the radical reaction were then determined, and X-ray crystal structure analyses were carried out on the reaction products. The different stereoselectivities in both cases are explained by different orientations of the menthyloxy substituent.
Référence
J Org Chem. 2004 Mar 5;69(5):1646-51.