Synthesis of Highly Functionalized Stable Heterocyclic Phosphorus Ylides. Cycloaddition Reaction between Conjugated Phosphorus Ylides and Alkyl Propiolates

✍ Scribed by Issa Yavari; Farahnaz Nourmohammadian

• Book ID: 104202768
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 83 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00400-2

✦ Synopsis

AbstractÐProtonation of the reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by 3-chlorotetrahydrofuran-2,4-dione leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the CH-acid to produce highly functionalized phosphorus ylides containing a furandione ring system in excellent yields. Using alkyl propiolates, the corresponding phosphorus ylides are formed and undergo [412] cycloaddition reaction with the alkyl propiolates to produce hitherto unknown furo[2,3-b]pyran ring systems in good yields.