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Lewis Acid-Mediated Decarboxylative Allylation of Enol Carbonates
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2021-05-17 , DOI: 10.1002/hlca.202100065 Tohru Yamada 1 , Kodai Saito 2 , Yoichi Dokai 2 , Takuma Nishizawa 3
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2021-05-17 , DOI: 10.1002/hlca.202100065 Tohru Yamada 1 , Kodai Saito 2 , Yoichi Dokai 2 , Takuma Nishizawa 3
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A homoallylic ketone can be transformed and functionalized by various synthetic reactions, and thus, is regarded as one of the representative building blocks in organic chemistry. An additional route to access homoallylic ketones, namely, a Lewis acid-mediated decarboxylative allylation of cyclic enol carbonates, prepared by fixation of carbon dioxide onto propargyl alcohols, was developed in this work. The treatment of a cyclic enol carbonate with a Lewis acid in the presence of an allylsilane resulted in the formation of a homoallylic ketone. It was found that the title reaction proceeded well by the combined use of zirconium tetrachloride with allyltrimethylsilane. The allylation occurred with high regioselectivity and the corresponding homoallylic ketones were obtained in good-to-high yields. A reaction mechanism involving the decarboxylative formation of an oxyallyl cation equivalent is proposed.
中文翻译：
路易斯酸介导的烯醇碳酸酯的脱羧烯丙基化
高烯丙基酮可以通过各种合成反应进行转化和官能化，因此被认为是有机化学中的代表性构件之一。在这项工作中开发了另一种获得高烯丙基酮的途径，即路易斯酸介导的环状烯醇碳酸酯的脱羧烯丙基化，通过将二氧化碳固定在炔丙醇上而制备。用路易斯处理环状烯醇碳酸酯在烯丙基硅烷的存在下，酸导致高烯丙基酮的形成。发现通过四氯化锆与烯丙基三甲基硅烷的组合使用，标题反应进行得很好。烯丙基化反应以高区域选择性发生，相应的同烯丙基酮以良好到高的产率获得。提出了涉及氧烯丙基阳离子等价物脱羧形成的反应机制。
更新日期：2021-07-16
中文翻译：
路易斯酸介导的烯醇碳酸酯的脱羧烯丙基化
高烯丙基酮可以通过各种合成反应进行转化和官能化，因此被认为是有机化学中的代表性构件之一。在这项工作中开发了另一种获得高烯丙基酮的途径，即路易斯酸介导的环状烯醇碳酸酯的脱羧烯丙基化，通过将二氧化碳固定在炔丙醇上而制备。用路易斯处理环状烯醇碳酸酯在烯丙基硅烷的存在下，酸导致高烯丙基酮的形成。发现通过四氯化锆与烯丙基三甲基硅烷的组合使用，标题反应进行得很好。烯丙基化反应以高区域选择性发生，相应的同烯丙基酮以良好到高的产率获得。提出了涉及氧烯丙基阳离子等价物脱羧形成的反应机制。
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