Upgrading malic acid to bio-based benzoates via a Diels–Alder-initiated sequence with the methyl coumalate platform?
RSC Advances Pub Date: 2014-09-15 DOI: 10.1039/C4RA07105K
Abstract
The conversion of naturally-occurring malic acid to the 2-pyrone methyl coumalate was optimized using a variety of acid catalysts. Coupling methyl coumalate with electron-rich dienophiles in an inverse electron-demand Diels–Alder (IEDDA)/decarboxylation/elimination domino sequence resulted in an investigation of the scope and limitations of the methodology. The thermal, metal-free, and one-pot procedure allows regioselective access to diverse aromatic compounds including tricyclic, biphenyl, and pyridinyl systems for elaboration. A comparison with analogous pyrones demonstrates the striking efficacy of methyl coumalate as a versatile platform for the generation of biorenewable functionalized benzoates.
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Journal Name：RSC Advances
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CAS no.: 89640-58-4
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