手性布朗斯特酸催化通过形式上的[3 + 2]环加成对螺异吲哚啉酮 - 二氢吲哚进行对映选择性合成。
Chiral Brønsted Acid Catalyzed Enantioselective Synthesis of Spiro-Isoindolinone-Indolines via Formal [3 + 2] Cycloaddition.
作者信息
Unhale Rajshekhar A, Sadhu Milon M, Singh Vinod K
机构信息
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, Madhya Pradesh 462 066, India.
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India.
出版信息
Org Lett. 2022 May 13;24(18):3319-3324. doi: 10.1021/acs.orglett.2c00748. Epub 2022 May 4.
A novel organocatalytic asymmetric formal [3 + 2] cycloaddition of 3-substituted 1H-indoles with in situ generated 3-hydroxy-isoindolinone-derived β,γ-alkynyl-α-ketimines has been developed. A variety of biologically relevant chiral spiro-isoindolinone-indolines were achieved with excellent yields (up to 99%) and enantioselectivity (up to 99% ee) under mild conditions. The gram-scale reaction of this methodology and several interesting transformations of the products have been demonstrated.
已开发出一种新型有机催化的3-取代1H-吲哚与原位生成的3-羟基异吲哚啉酮衍生的β,γ-炔基-α-酮亚胺的不对称形式[3 + 2]环加成反应。在温和条件下，以优异的产率（高达99%）和对映选择性（高达99% ee）得到了多种具有生物学相关性的手性螺异吲哚啉酮-吲哚啉。已证明了该方法的克级反应以及产物的几种有趣转化。
Zotero 插件