Tetrahedron p. 5883 - 5900 (1992)
Update date:2022-08-04
Topics:
Celli, Angela M.
Scotton, Mirella
Sega, Alessandro
The hetero-Diels-Alder reaction of 1-oxabutadienes 1a-c bearing electron-withdrawing groups with ethyl vinyl ether and 2,3-dihydrofuran gave the functionalized 5,6-dihydro-4H-pyrans 2a-c, 4c and 4H-4a,5,6,6a-tetrahydrofuro<2,3-b>pyrans 5a-c and 6c.Cycloadducts 2a and 4c easily rearranged to furo<2,3-b>furans 3a, 3c and 9c and cycloadducts 5a and 6c to difuro<2,3-b:3',4'-d>furans 7a, 7c and 8c.The stereochemistry of the compounds 5c and 7a was determined by single crystal X-ray analysis.Relative configurations of the other compounds were established by nOe data.Some aspects of the reaction mechanisms are discussed. Key Words: furo-furans, furo-pyrans, hetero-Diels-Alder, nOes.
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Doi:10.1016/S0040-4020(01)86311-0
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(1992)
