Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of α-Nitrocinnamate

A systematic study of the Diels–Alder reaction α-nitrocinnamate was performed. The p-substituted with 2,3-dimethyl-1,3-butadienes smoothly proceeded regardless p-substituent, which either an electron-donating or -withdrawing group. control revealed that isomerized during reaction. Danishefsly’s diene (1-methoxy-3-trimethylsiloxy-1,3-butadiene) facilitated cycloaddition under mild conditions to afford a cycloadduct without alternation diastereomeric ratio. Moreover, desilylation furnished multiple functionalized cyclohexanones.