Tetrahedron Asymmetry p. 1247 - 1262 (1991)
Update date:2022-07-31
Topics:
Jong, Johannes C. de
Bolhuis, Fre van
Feringa, Ben L.
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.
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