A catalytic approach to the base-promoted reaction of epoxides with activated methylenes

✍ Scribed by Tommaso Angelini; Francesco Fringuelli; Daniela Lanari; Ferdinando Pizzo; Luigi Vaccaro

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 819 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.01.055

✦ Synopsis

This contribution reports the results obtained in the definition of a catalytic method for the nucleophilic ring opening of epoxides by activated methylenes promoted by a polymer-supported base. The attention has been focused on the use of polymer supported bases and the best results have been obtained by using 4-(dimethylamino)pyridine (PS-DMAP) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine both on polystyrene (PS-BEMP). Solvent-free conditions has been essential for reaching a sufficient reactivity to realize this process, in fact when a reaction medium is used, the processes are almost unfeasible.