Synthesis of Bio-Derived Cyclic Carbonates from Renewable Resources

The coupling reaction of carbon dioxide and terminal,
internal,
and highly substituted epoxides derived from renewable resources such
as furfural, limonene, carvone, carvyl acetate, terpinen-4-ol, or
ionone leads to the synthesis of new bioderived cyclic carbonates
using an efficient aluminum catalyst under mild and solvent-free reaction
conditions. Interestingly, the synthesis of highly substituted bioderived
cyclic carbonates can occur with excellent diastereoselectivity, obtaining
in some cases one diastereoisomer as the major product. The X-ray
crystal structures of two enantiomerically pure carvone-based cyclic
carbonates are reported.