Transition metal-free strategies for the stereoselective construction of spirocyclopropyl oxindoles

TETRAHEDRON

卷:76

Article

Bacher, Emily P.¹  Ashfeld, Brandon L.¹ 

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

关键词: Cyclopropanation;    Spirooxindole;    Diastereoselective;    Metal-free;    Enantioselective;   

DOI  :  10.1016/j.tet.2019.130692

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free