铜催化的 Grignard 试剂与原位生成的吲哚衍生的烯胺的加成反应。
Copper-Catalyzed Addition of Grignard Reagents to in situ Generated Indole-Derived Vinylogous Imines.
机构信息
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
出版信息
Chemistry. 2020 Dec 9;26(69):16277-16280. doi: 10.1002/chem.202004232. Epub 2020 Nov 9.
Abstract
Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3-sec-alkyl-substituted indoles in high yields and enantiomeric ratios is presented. This methodology makes use of a chiral catalyst based on copper phosphoramidite complexes and in situ formation of vinylogous imine intermediates.
摘要
手性吲哚衍生物在药物和生物碱中普遍存在。本文首次报道了手性铜膦亚胺催化剂促进的格氏试剂与各种磺酰吲哚的不对称共轭加成反应，为合成高收率和对映选择性的 3-位取代的手性吲哚提供了一种简洁的方法。该方法利用了手性铜磷酰胺配合物催化剂和原位形成的烯醇亚胺中间体。
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