Synthesis of novel 2H,5H-dihydrofuran-3-yl ketones via ISNC reactions

✍ Scribed by Matthew L. Grandbois; Kelsie J. Betsch; William D. Buchanan; Jetty L. Duffy-Matzner

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 230 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.08.110

✦ Synopsis

Unique 1-[2H,5H-dihydrofur-3-yl]ketones have been synthesized from propargylic nitroethers via intramolecular cycloadditions involving silyl nitronates. Various substituent groups were placed on the 2 and 5 positions of the dihydrofuran rings. We examined the scope of the long-range coupling in proton NMR of the oxo-dihydrofuran products. The identities of the diastereomers resulting from the Michael Addition/cycloaddition reactions were tentatively assigned for the first time. CAChe MNDO PM5 and CONFLEX programs were engaged to assist with the identification of these stereoisomers. The reaction times and conditions for these oxo-dihydrofurans were found to be different than that of the published dihydrofuranals, which led us to propose a different mechanism.