Palladium‐Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols. (16th February 2017)

• Record Type: Journal Article
• Authors: Qiu, Youai; Yang, Bin; Jiang, Tuo; Zhu, Can; Bäckvall, Jan‐E.
• Is Part Of: Angewandte Chemie. Volume 129:Number 12(2017)
• Page Start: 3269
• Page End: 3273
• Publication Date: 2017-02-16
• Subjects: Carbocyclisierungen -- Enallenole -- Oxidationen -- Palladium -- Spirolactone; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201612384
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A highly selective palladium‐catalyzed oxidative carbonylation/carbocyclization/alkoxycarbonylation of enallenols to afford spirolactones bearing an all‐carbon quaternary center was developed. This transformation involves the overall formation of three C−C bonds and one C−O bond through a cascade insertion of carbon monoxide (CO), an olefin, and CO. Preliminary experiments on chiral anion‐induced enantioselective carbonylation/carbocyclization of enallenols afforded spirolactones with moderate enantioselectivity.