ASYMMETRIC DIELS-ALDER REACTIONS. INVERSE ELECTRON DEMAND REACTIONS OF ESTERS OF 2-HYDROXYPYRAN-2-ONE WITH VINYL ETHERS: USE OF HIGH PRESSURE TO AVOID DECARBOXYLATION OF ADDUCTS

Article abstract of DOI:10.1016/S0040-4039(00)79707-3

Asymmetric inverse electron-demand Diels-Alder reactions of esters of 3-hydroxypyran-2-one with vinyl ethers proceed under high pressure at ambient temperature, making isolation of the synthetically useful bicyclic adducts feasible.Investigation has revealed that the desired adduct can be synthesized with diastereofacial selectivity, up to 88:12, by reaction of the acetate of 3-hydroxypyran-2-one with chiral 8-(3,5-dimethylphenyl)menthyl vinyl ether.