Stereoelectronic control in the solvolysis of spiroepoxidic 1-norbornyl triflates: unexpected reactivity in 3-bromomethyl derivatives

✍ Scribed by Antonio García Martínez; Enrique Teso Vilar; Amelia García Fraile; Santiago de la Moya Cerero; Cristina Díaz Morillo

• Book ID: 104098927
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 418 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.02.006

✦ Synopsis

a b s t r a c t

Interesting norbornane-fused tetrahydrofurans, with an additional synthetically-valuable vicinal dioxysubstitution in the norbornane skeleton, are enantiospecifically obtained in high yield from epimeric camphor-derived 3-endo-bromomethyl-substituted spiroepoxidic 1-norbornyl triflates. The process takes place via a domino reaction stereoelectronically controlled by the bromine atom. The described process has synthetic value, since it opens the way for a future enantiospecific preparation of 2,3-disubstituted tetrahydrofurans from camphor.