Asymmetric N-Hydroxyalkylation of Indoles with Ethyl Glyoxalates Catalyzed by a Chiral Phosphoric Acid: Highly Enantioselective Synthesis of Chiral N,O-Aminal Indole Derivatives
Asymmetric N-Hydroxyalkylation of Indoles with Ethyl Glyoxalates Catalyzed by a Chiral Phosphoric Acid: Highly Enantioselective Synthesis of Chiral N,O-Aminal Indole Derivatives
复制标题
手性磷酸催化乙醛酸乙酯对吲哚的不对称 N-羟烷基化：手性 N,O-氨基吲哚衍生物的高度对映选择性合成
DOI：
10.1021/acs.orglett.9b00757
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Zhang Shu Yu
中科院分区：
文献类型：
--
作者：
Wang Le;Zhou Jia;Ding Tong Mei;Yan Zhi Qiang;Hou Si Hua;Zhu Guo Dong;Zhang Shu Yu
本文报道了一种由spinol衍生的手性磷酸催化多取代吲哚与乙草酸酯不对称分子间n -羟基烷基化的方法。该方案提供了一种替代的，方便的，直接的策略，有效地获得结构独特的α-手性吲哚，o -无环动物，具有广泛的底物范围和良好的对映选择性。通过克级实验和随后更复杂的手性n， o -氨基吲哚衍生物的有效合成，说明了这种方法的合成效用。
A method of SPINOL-derived chiral phosphoric acid catalyzed asymmetric intermolecularN-hydroxyalkylation of multisubstituted indoles with ethyl glyoxalates is described in this report. This protocol provides an alternative, convenient, and direct strategy for efficient access to structurally unique α-chiral indoleN,O-acyclic aminals with a broad substrate scope and good to excellent enantioselectivities. The synthetic utility of this methodology is illustrated by a gram-scale experiment and the subsequent efficient synthesis of more complex chiralN,O-aminal indole derivatives.