Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Kumar, Amit; Vachhani, Dipak D.; Modha, Sachin G.; Sharma, Sunil K.; Parmar, Virinder S.; Eycken, Erik V. Van der

doi:10.3762/bjoc.9.246

Cited by 48 publications

(25 citation statements)

References 64 publications

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“…33,34 The developed post-Ugi, Au(I)-catalyzed diastereoselective domino cyclization process involved a ''branched-handed'' pre-cyclization architecture resulting from the chiral center present in the Ugi adduct 81. The expected outcome of the reaction was an indoloazepinone through an endo-dig cyclization and rearrangement sequence.…”

Section: View Article Onlinementioning

confidence: 99%

“…[32][33][34] To access such alkaloids in a one pot cascade fashion and securing diversity is highly desirable from the viewpoint of sustainable chemistry. The first one-pot multicomponent attempt towards such complex alkaloids was reported by El Kaïm and co-workers 32 whereby spirocyclization was achieved using a stoichiometric amount of Cu(II) salt in refluxing DBU-THF system.…”

Section: View Article Onlinementioning

confidence: 99%

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Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

et al. 2015

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The Ugi-4CR is by far one of the most successful multicomponent reactions leading to high structural diversity and molecular complexity. However, the reaction mostly affords a linear peptide backbone, enabling post-Ugi transformations as the only solution to rigidify the Ugi-adduct into more drug like species. Not surprisingly, the development of these transformations, leading to new structural frameworks, has expanded rapidly over the last few years. As expected, palladium-catalyzed reactions have received the foremost attention, yet other metals, particularly gold complexes, are fast catching up. This tutorial review outlines the developments achieved in the past decade, highlighting the modifications that are performed in a sequential or domino fashion with emphasis on major concepts, synthetic applications of the derived products as well as mechanistic aspects.

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Section: View Article Onlinementioning

confidence: 99%

Section: View Article Onlinementioning

confidence: 99%

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

et al. 2015

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“…Thereafter, the same group has developed reusable supported gold nanoparticles to catalyze this transformation under batch and microflow settings. In addition, an analogous transformation has been documented for Ugi substrates that were obtained using propargylamines as a triple bond source …”

Section: Scope Comparison Of the Previous And Current Protocols For Tmentioning

confidence: 97%

Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines

et al. 2019

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A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation.

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“…这与之前的文献报道的策略不同, 采用此处的"branched-handed"策略, 即 C3 边链分支成两条边链, 分别含有炔基和分子内亲核试剂(Scheme 23A). 2013 年, Van der Eycken 小组 [42] [49] 使用色胺或色醇 77 作为底物, 在手性金络合物催化剂存在下, 与联烯酰胺 75 反应, 以中等到优秀的对映选择性快速构建吡咯吲哚啉类化合物 78 (Scheme 27). 在之前的金催化吲哚分子间去芳构化生成亚铵中间体 28-A 经历质子去金化而生成最终产物 [48] .…”

Section: 分子内反应unclassified

Recent Progress on Gold-catalyzed Dearomatization Reactions

Wu¹,

Zhang²,

You³

2017

Acta Chim. Sinica

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Homogeneous gold catalysis has experienced rapid development since 2004 and generally exhibited high efficiency and good functional group tolerance. On the other hand, catalytic dearomatization reactions provide a unique and straight approach to the construction of highly functionalized molecules with diverse three-dimensional structures from simple aromatic compounds. In this perspective, recent examples on gold-catalyzed dearomatization reactions are summarized in two main categories: gold-catalyzed rearrangements and gold-catalyzed hydrofunctionalizations of alkynes and allenes. In the first category, intra-and inter-molecular dearomatization reactions were achieved via gold-catalyzed rearrangements of propargylic ester and its derivatives. Although this area is still at its early stage, several outstanding asymmetric examples have been reported by Shi and Toste. In the second category, an array of dearomatization reactions via gold-catalyzed hydrofunctionalizations of alkynes and allenes were presented. All these cases have shown great potentials for convenient and straightforward construction of spiro and/or bridged polycyclic molecules, and some of them have exhibited excellent enantioselectivity. In addition, salient features and proposed mechanisms for these two types of reactions are also described.

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Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Cited by 48 publications

References 64 publications

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines

Recent Progress on Gold-catalyzed Dearomatization Reactions

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