Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position

Abstract

The 3,3'-disubstituted oxindole structural motif is a prominent feature in many alkaloid natural products, which include all kinds of tetrasubstituted carbon stereocenters, spirocyclic or not, all-carbon or heteroatom-containing. The catalytic asymmetric synthesis of the tetrasubstituted carbon stereocenter at the C-3 position of the oxindole framework integrates new synthetic methods and chiral catalysts, reflects the latest achievements in asymmetric catalysis, and facilitates the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. This review summarizes the recent progress in this area, and applications in the total synthesis of related bioactive compounds.

Palladium(0)-Catalyzed Benzylic C(<i>sp</i>³)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

“…Spirooxindole natural products, which are characterized by the fused spiro-structure of their oxindole core bearing various rings at its C3 position, have attracted considerable attention from numerous synthetic chemistry groups because of their complex structures and their pronounced biological activities [44][45][46][47][48][49][50][51][52][53] (Fig. 1).…”

Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

“…Keywords C-H functionalization; oxindoles; cascade reaction 吲哚酮骨架结构广泛存在于天然产物、药物和农药 分子结构中, 其中 C(3)双取代的吲哚酮化合物具有抗肿 瘤、 抗心血管疾病等重要的生物活性作用(图 1) [1] . 因此, 有关该类化合物的构建方法研究引起有机和药物化学 工作者的极大关注 [2] . 例如光学纯的 C(3)双取代吲哚酮 衍生物的制备可以通过靛红与亲核试剂的不对称催化 反应得以实现 [3] .…”

Theoretical Studies of Colvent Effect for Oxindole Derivatives Using Polarizable Continuum Model

“…Oxindole frameworks are found in many bioactive compounds and natural products. Due to this synthetic methods and transformations of oxindole skeletons have been extensively investigated [2][3][4][5] . The naturally occurring oxindole derivative convolutamydine has been found to exhibit potent activity in the differentiation of HL-60 human plomyelocyticleukemic cells.…”