期刊
CHEMSUSCHEM
卷 13, 期 19, 页码 5213-5219出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202001471
关键词
acetals; Diels-Alder; drug delivery; hydroxymethylfurfural; maleimides
资金
- Great Lakes Bioenergy Research Center, U.S. Department of Energy, Office of Science, Office of Biological and Environmental Research [DE-SC0018409]
- U.S. Department of Energy [DE-EE0008353]
Catalytic strategies were developed to synthesize and release chemicals for applications in fine chemicals, such as drugs and polymers, from a biomass-derived chemical, 5-hydroxymethyl furfural (HMF). The combination of the diene and aldehyde functionalities in HMF enabled catalytic production of acetalized HMF derivatives with diol or epoxy reactants to allow reversible synthesis of norcantharimide derivatives upon Diels-Alder reaction with maleimides. Reverse-conversion of the acetal group to an aldehyde yielded mismatches of the molecular orbitals in norcantharimides to trigger retro Diels-Alder reaction at ambient temperatures and released reactants from the coupled molecules under acidic conditions. These strategies provide for the facile synthesis and controlled release of high-value chemicals.
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