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Palladium‐Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols
Author(s) -
Qiu Youai,
Yang Bin,
Jiang Tuo,
Zhu Can,
Bäckvall JanE.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612384
Subject(s) - carbonylation , palladium , chemistry , catalysis , carbon monoxide , olefin fiber , enantioselective synthesis , oxidative phosphorylation , cascade , monoxide , combinatorial chemistry , cascade reaction , oxidative addition , organic chemistry , biochemistry , chromatography
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.