Catalytic Enantioselective γ-Selective Additions of 2-Allylazaarenes to Activated Ketones
Catalytic Enantioselective γ-Selective Additions of 2-Allylazaarenes to Activated Ketones
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DOI：
10.1002/anie.201700190
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发表时间：
2017-03-20
影响因子：
16.6
通讯作者：
Jiang, Zhiyong
中科院分区：
文献类型：
--
作者：
Bai, Xiangbin;Zeng, Guangkuo;Jiang, Zhiyong
本文报道了2-烯丙基氮杂芳烃在不对称催化中的第一个实例。高g-选择性烯丙基化被证明为活化酮，包括靛红和三氟甲基酮。在氨基酸基叔胺或季铵盐催化剂的存在下，两个系列的含叔羟基的结构部分以良好的化学产率、优异的对映选择性和E/Z比安装在氮杂芳烃的远端δ-位置。目前的γ-选择性反应的成功应该为扩展到其他烯丙基氮杂芳烃衍生物提供灵感，并将为手性γ-和/或δ-官能化氮杂芳烃的合成开辟新的范例。
Reported herein is the first example of 2-allylazaarenes in asymmetric catalysis. Highly g-selective allylation was demonstrated for activated ketones, including isatins and trifluoromethyl ketones. In the presence of either an amino-acid-based tertiary amine or quaternary ammonium salt catalyst, two series of tertiary hydroxy-containing moieties were installed at the remote delta-position of azaarenes in good chemical yields, excellent enantioselectivities, and E/Z ratios. The success of current gamma-selective reactions should provide inspiration for expansion to other allylazaarene derivatives and would open up new paradigms for the synthesis of chiral gamma- and/or delta-functionalized azaarenes.