First general approach to cyclohex-3-ene-1, 1-bis (phosphonates) by Diels-Alder cycloaddition of tetraethyl vinylidenebis (phosphonate) to 1, 3-dienes

…, G Ricci, A Gioiello, H Couthon-Gourves…

文献索引：Ruzziconi, Renzo; Ricci, Giacomo; Gioiello, Antimo; Couthon-Gourves, Helene; Gourves, Jean-Philippe Journal of Organic Chemistry, 2003 , vol. 68, # 3 p. 736 - 742

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被引用次数: 19

摘要

Tetraethyl vinylidenebis (phosphonate)(VBP) reacts smoothly with substituted 1, 3-dienes at 90-110° C without solvent to give the corresponding cyclohex-3-ene-1, 1-bis (phosphonates) in good yields (60-85%). With nonsymmetrically substituted dienes, mixtures of regioisomers are obtained, the regioisomeric ratio being exclusively controlled by electronic effects. Danishefsky's diene allows tetraethyl 4-oxocyclohex-2-ene-1, 1-bis ( ...