Synthesis of hydronaphthalenes through coupling of enyne-carbonyl compounds that contain pendant alkane groups with Fischer carbene complexes

✍ Scribed by Rajesh Kumar Patti; Shaofeng Duan; Alejandro Camacho-Davila; Kris Waynant; Kenneth A. Dunn; James W. Herndon

• Book ID: 104097844
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 370 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.05.049

✦ Synopsis

The coupling of enyne-carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes to afford furans that contain pendant alkene groups is described. Subsequent intramolecular Diels-Alder reactions are effective in selected cases, resulting in hydronaphthalene systems after dehydration. Although the Diels-Alder event is thermodynamically unfavorable, the overall transformation of alkene-furans to dihydronaphthalenes is a favorable process.