Abstract
The addition of lithiated alkoxyallenes to carbonyl compounds furnishes allenyl alcohols, which undergo a highly efficient and chemoselective 5-endo-trig cyclization to 3-alkoxy-2,5-dihydrofurans catalyzed by gold(I) chloride. The dihydrofurans produced can be either oxidized to β-alkoxy butenolides by a manganese(III) acetate catalyzed radical oxidation with tert-butyl hydroperoxide, or transformed into α,β-unsaturated γ-keto aldehydes by an oxidative ring cleavage using DDQ in the presence of water. Treatment of the γ-keto aldehydes with sodium methoxide in methanol promotes a diastereoselective intramolecular aldol addition furnishing alkoxy-substituted cyclopentenone derivatives in good yield.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
