Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of -Nitrocinnamate by Takumi Hamada Kento Iwai & Nagatoshi Nishiwaki

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


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