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

Reactions Pub Date : 2022-12-02 DOI:10.3390/reactions3040041
Takumi Hamada, Kento Iwai, N. Nishiwaki
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引用次数: 0

Abstract

A systematic study of the Diels–Alder reaction of α-nitrocinnamate was performed. The reaction of p-substituted α-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 α-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.
α-硝基氨基酸酯diols - alder反应合成多功能化环己酮及表征
对α-硝基氨基酸酯的Diels-Alder反应进行了系统的研究。对取代α-硝基酸酯与2,3-二甲基-1,3-丁二烯的反应顺利进行,无论其取代基是供电子基还是吸电子基。对照反应表明α-硝基氨基甲酸酯在反应过程中异构化。Danishefsly的二烯(1-甲氧基-3-三甲基硅氧基-1,3-丁二烯)在温和的条件下可以在不改变非对映比的情况下生成环加合物。此外,环加合物的脱硅化反应提供了多个功能化的环己酮。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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CiteScore
2.70
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