Chretien, J.-M., Zammattio, F., Gauthier, D., Le Grognec, E., Paris, M. & Quintard, J.-P. (2006) Preparation of allyltin reagents grafted on solid support: Clean and easily recyclable reagents for allylation of aldehydes. Chem.-Eur. J. 12 6816–6828.
Added by: Florent Boucher (2016-05-12 13:21:36) |
Type de référence: Article DOI: 10.1002/chem.200501595 Numéro d'identification (ISBN etc.): 0947-6539 Clé BibTeX: Chretien2006 Voir tous les détails bibliographiques |
Catégories: IMN Mots-clés: acid mediated reduction, aldehydes, allylation, asymmetric-synthesis, carbon bond formation, cross-linked polystyrene, diastereoselective synthesis, homoallylic alcohols, lewis-acid, olefin-metathesis, organotin reagents, palladium catalyst, polymer-supported reagents, Recycling, tin Créateurs: Chretien, Gauthier, Le Grognec, Paris, Quintard, Zammattio Collection: Chem.-Eur. J. |
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Résumé |
The preparation of polymer-supported allyltin reagents was shown to be possible for both unfunctionalized and functionalized allyl units. These reagents were treated with aldehydes in the presence of cerium(m) or indium(m) salts to afford high yields of homoallylic alcohols, practically uncontaminated with organotin residues (less than 5 ppm). Some mechanism aspects are briefly discussed and the potential for regeneration and reuse of these supported reagents is pointed out.
Added by: Florent Boucher |