Transition metal-free strategies for the stereoselective construction of spirocyclopropyl oxindoles
Transition metal-free strategies for the stereoselective construction of spirocyclopropyl oxindoles
复制标题
DOI：
10.1016/j.tet.2019.130692
复制
发表时间：
2020-01-24
期刊：
影响因子：
2.1
通讯作者：
Ashfeld, Brandon L.
中科院分区：
文献类型：
--
作者：
Bacher, Emily P.;Ashfeld, Brandon L.
螺环丙基氧吲哚基序是一种重要的结构亚基，作为一种成熟的药效团存在于许多具有生物活性的天然产物和小分子中，应用于广泛的治疗领域。因此，对该核心框架的立体选择性组装的努力在最近无金属环加成策略的复苏中发挥了作用。本文综述了近年来制备螺环丙基氧吲哚骨架的无过渡金属方法，这些方法具有高水平的非对映选择性，分为三种基于试剂的分类：1)采用重氮化合物的环丙烷化，2)pl3介导的环丙烷化，以及3)有机催化的形式[2 + 1]-环加成。(C) 2019 Elsevier Ltd.版权所有。
The spirocyclopropyl oxindole motif is an important architectural subunit as a well-established pharmacophore that is present in many biologically active natural products and small molecules with applications across a wide array of therapeutic areas. As a result, efforts toward the stereoselective assembly of this core framework have played a role in the recent resurgence of metal-free cycloaddition strategies. This review covers those recent transition metal-free approaches to the spirocyclopropyl oxindole framework proceeding with high levels of diastereoselectivity as classified into three reagent-based classifications: 1) cyclopropanations employing diazo compounds, 2) PL3-mediated cyclopropanations, and 3) organocatalyzed formal [2 + 1]-cycloadditions. (C) 2019 Elsevier Ltd. All rights reserved.