期刊
CHEMICAL SCIENCE
卷 6, 期 8, 页码 4479-4483出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01553g
关键词
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资金
- UC Irvine
- National Institutes of Health [GM105938]
- Eli Lilly
- NSERC of Canada
We describe a Rh-catalyzed desymmetrization of all-carbon quaternary centers from alpha,alpha-bis(allyl)aldehydes by a cascade featuring isomerization and hydroacylation. This desymmetrization competes with two other novel olefin functionalizations that are triggered by C-H bond activation, including carboacylation and bisacylation. A BIPHEP ligand promotes enantioselective formation of alpha-vinylcyclopentanones. Mechanistic studies support irreversible and enantioselective olefin-isomerization followed by olefin-hydroacylation.
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