Asymmetric Diels-Alder Reactions with 5-Menthyloxy-2(5H)-furanone

Article abstract of DOI:10.1016/S0957-4166(00)80024-5

A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed.Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol.Excellent diastereoselectivities (d.e. <*>99percent) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes.The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.