Cycloaddition Reactions of Phosphate Dienes

Article abstract of DOI:10.1021/jo00245a030

A series of phosphate dienes has been prepared and tested in 4 + 2 cycloadditions with representative dienophiles such as maleic anhydride and cyclohexenone.The most reactive diene in this series, bis(2,6-dimethoxyphenyl) 1-methylene-2-propenyl phosphate (14), displays a reactivity and regioselectivity comparable to the analogous (trimethylsilyl)oxy diene in its reactions with these dienophiles.However, phosphate dienes may offer distinct advantages in a synthetic sequence, especially when coupled with the methodology recently developed for preparing β-keto phosphonates from cyclic vinyl phosphates.