手性布朗斯特酸催化吲哚与伯醇的分子内不对称烯丙基烷基化反应
Chiral Brønsted Acid-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Indoles with Primary Alcohols.
作者信息
Zou Lei-Ming, Huang Xian-Yun, Zheng Chao, Cheng Yuan-Zheng, You Shu-Li
机构信息
School of Pharmacy, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
出版信息
Org Lett. 2022 May 20;24(19):3544-3548. doi: 10.1021/acs.orglett.2c01253. Epub 2022 May 9.
Herein, chiral Brønsted acid-catalyzed intramolecular asymmetric allylic alkylation of indoles with allylic primary alcohols is described. The allyl alcohols were directly employed as the allylic precursors in this metal-free protocol, without preactivation or any additional activating reagents. This method provides the convenient synthesis of a broad range of functionalized tetrahydrocarbazoles in excellent yields (≤97%) with good enantioselectivity (≤93% ee). The optimal conditions are compatible for gram-scale reaction.
本文描述了手性布朗斯特酸催化吲哚与烯丙基伯醇的分子内不对称烯丙基烷基化反应。在这个无金属体系中，烯丙醇直接用作烯丙基前体，无需预活化或任何额外的活化试剂。该方法能以优异的产率（≤97%）和良好的对映选择性（≤93% ee）方便地合成多种功能化的四氢咔唑。最佳条件适用于克级规模的反应。
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