Organo-Catalyzed Regio- and Geometry-Specific Construction of β‑Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications
Organo-Catalyzed Regio- and Geometry-Specific Construction of β‑Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications
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有机催化的β-羟基-α-乙烯基羧酸酯的区域和几何结构特异性构建：底物范围、机理见解和应用
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发表时间：
2018
期刊：
影响因子：
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通讯作者：
Qi Zhang
中科院分区：
文献类型：
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作者：
Yonghai Chai;JinJin Zhou;Yanbin Wu;Yingle Feng;Panru Wang;Yange Chen;Xinying Wang;Beibei Zhao;Qi Zhang
提出了一种绿色合成β-羟基-α-乙烯基羧酸酯的方法，该方法是以含有活化α，β质子的醛和γ-不饱和酯为起始原料，在−−-Hillman反应条件下进行的。各种不同的β-羟基-α-乙烯基羧酸酯已在特定的区域以中等到较好的产率合成，只有E几何选择性。其他显著的特点包括原子效率、环境友好和温和的反应条件。此外，反应产物可以很容易地转化为四氢呋喃、二氢呋喃和呋喃衍生物。
A green protocol has been developed for the synthesis of β-hydroxyl-α-vinyl carboxylic esters using aldehydes and α,β-unsaturated esters bearing an activated γ proton as starting materials under Morita−Baylis−Hillman (MBH) reaction conditions. Diverse β-hydroxyl-α-vinyl carboxylic esters have been synthesized regiospecifically in moderate to good yields with only E geometric selectivity. Other remarkable features include atom efficiency, environmental.benignancy, and mild reaction conditions. Furthermore, the reaction products could be readily converted into tetrahydrofuran, dihydrofuran, and furan derivatives.