Premium
Direct Conversion of Activated 5‐Hydroxymethylfurfural into δ‐Lactone‐Fused Cyclopentenones
Author(s) -
Gomes Rafael F. A.,
Coelho Jaime A. S.,
Afonso Carlos A. M.
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802537
Subject(s) - furfural , chemistry , hydroxymethylfurfural , 5 hydroxymethylfurfural , organic chemistry , lactone , catalysis , raw material , decomposition
Valorization of biomass derived feedstock (e.g., 5‐hydroxymethylfurfural platform) is a very active field of chemical research. In this study, 5‐hydroxymethylfurfural is converted into cyclopenten‐2‐ones by virtue of furfural's activation and Meldrum's acid's tendency to undergo decomposition/esterification. Experimental and computational studies suggest a domino rearrangement–lactonization reaction involving BINOL‐catalyzed lactonization as the rate‐determining step. The novel lactone‐fused cyclopenten‐2‐ones, which bear a quaternary carbon and resemble a didemnenone natural product structure, are converted into several derivatives with potential interest for the fields of synthetic and medicinal chemistry.