期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 15, 期 10, 页码 -出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00131b
关键词
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资金
- NSFC [21002043, 21272107]
- National S&T Major Project of China [2012ZX09504-001-003]
- Fundamental Research Funds for the Central Universities [2022016zr0064]
This work concerns the Mg(OMe)(2) promoted allylic isomerization of gamma-hydroxy-alpha,beta-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded gamma-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-gamma-hydroxy-alpha,beta-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible gamma-hydroxy-alpha,beta-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.
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