从 2-吡喃酮制备芳烃顺式二氢二醇的对映选择性合成。
Enantioselective Synthesis of Arene cis-Dihydrodiols from 2-Pyrones.
机构信息
Department of Chemistry and Research Center for Molecular Recognition and Synthesis, Fudan University, 220 Handan Rd., Shanghai, 200433, China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Rd., Shanghai, 200032, China.
出版信息
Angew Chem Int Ed Engl. 2019 Oct 7;58(41):14562-14567. doi: 10.1002/anie.201908284. Epub 2019 Aug 29.
An enantioselective chemical synthesis of arene cis-dihydrodiols has been realized from 2-pyrones through sequential ytterbium-catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and retro-Diels-Alder extrusion of CO . By using this strategy, a series of substituted arene cis-dihydrodiols can be obtained efficiently with high enantioselectivity (>99 % ee in many cases). Based on this strategy, efficient and concise asymmetric total syntheses of (+)-MK7607 and 1-epi-(+)-MK7607 were accomplished.
已实现从 2-吡喃酮通过铒催化不对称逆电子需求 Diels-Alder（IEDDA）反应和 CO 反-Diels-Alder 挤出的顺序反应，以对映选择性方式合成芳基顺式二氢二醇。通过使用这种策略，可以有效地获得一系列取代的芳基顺式二氢二醇，具有高对映选择性（在许多情况下>99％ee）。基于该策略，高效简洁地完成了（+）-MK7607 和 1-epi-（+）-MK7607 的不对称全合成。
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