Construction of Spirocyclic Oxindoles through Regio‐ and Stereoselective [3+2] or [3+2]/[4+2] Cascade Reaction of α,β‐Unsaturated Imines with 3‐Isothiocyanato Oxindole

Du, Dan; Xu, Qin; Li, Xiao-Ge; Shi, Min

doi:10.1002/chem.201600497

Cited by 36 publications

(9 citation statements)

References 111 publications

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“…In 2016, Min Shi et al reported regioselective and stereoselective [3+2] cascade reaction of ,-unsaturated imines 10 with 3-isothiocyanato oxindoles 11 to produce spirocyclic oxindole derivatives 12 and 13 (Scheme 3). 17…”

Section: Synthesis Of Oxindoles Skeletonmentioning

confidence: 99%

Recent Advances in [3+2]-Cycloaddition-Enabled Cascade Reactions: Application to Synthesize Complex Organic Frameworks

Erande¹,

Shivam²,

Chavan³

et al. 2022

Synlett

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Many natural products and biologically important complex organic scaffolds have convoluted structures around their core skeleton. Interestingly, with just changing the outskirts, the core reflects new and unique degrees of various physical and chemical properties. A very common but intriguing core is a five-membered ring horning heaps of organic molecules crafts. The power of [3+2] cycloaddition reactions to generate five-membered ring systems allocate chemists to envision synthetic procedures of wonder molecules and if it is facilitating a cascade sequence, then the end product will imbibe significant level of complexity having applications in medicinal and pharmaceutical fields. This Account highlights the broad interest in assembling recent advances in cascade reactions involving [3+2] cycloaddition as the power tool in order to conceive breakthrough organic architectures reported in the last ten years. We foresee that our comprehensive collection of astonishing [3+2] cycloaddition enabled cascades will provide valuable insights to polycyclic molecular construction and perseverant approach towards nonconventional synthetic procedures to the organic community.1 Introduction2 Synthesis of Oxindoles Skeleton3 Synthesis of Oxazoles Skeleton4 Synthesis of Oxadiazoles Skeleton5 Synthesis of Nitrogen-Containing Heterocycles6 Synthesis via Formal [3+2] Cycloaddition7 Synthesis of Miscellaneous Scaffolds8 Conclusion

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Section: Synthesis Of Oxindoles Skeletonmentioning

confidence: 99%

Recent Advances in [3+2]-Cycloaddition-Enabled Cascade Reactions: Application to Synthesize Complex Organic Frameworks

Erande¹,

Shivam²,

Chavan³

et al. 2022

Synlett

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“…In 2016, Shi's group studied the reactivity of different azadienes in the reaction with 3-Isothiocyanate oxindoles 42, catalysed by chiral bifunctional thioureas (Scheme 9) [30]. The α,βunsaturated imines 43, 45, and 47 were used as electrophiles to initiate the cascade sequence, followed by a thiolactam ring closure, which depended on the starting imine.…”

Section: Formal Cycloaddition Reactions With 3-isothiocyanate Oxindolesmentioning

confidence: 99%

Step Economy in the Stereoselective Synthesis of Functionalized Oxindoles via Organocatalytic Domino/One-pot Reactions

Bortolami¹

2021

COC

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Oxindoles are an important class of heterocyclic scaffolds widely present in natural products and bioactive compounds. For this reason, a plethora of methodologies for the stereoselective synthesis of enantioenriched oxindoles has been studied over the years. Among all the reported synthetic strategies, organocatalysis has proven to be a powerful tool for the asymmetric synthesis of this class of compounds being a step-and atom-economical, environmentally friendly, and non-toxic approach. This review will outline the application of asymmetric organocatalysis in the synthesis of chiral oxindole-based structures, relying on domino/one-pot reaction sequences in a step-economical fashion.

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“…These transformations can be conducted under mild organocatalytic conditions in a highly stereoselective manner. Thus, various mono-and bis-spiroheterocycles and their fused analogues have been constructed featuring thioimidazolidinone-spirooxindoles [26][27][28][29][30], fused-thioimidazolidinone-spirooxindoles [31], thiopyrrolidinone-spirooxindoles , fused-thiopyrrolidinone-spirooxindoles [53][54][55][56], thiooxazolidinone-spirooxindoles [57][58][59], and thio-1,2,4-triazolidinone [60].…”

Section: Introductionmentioning

confidence: 99%

Double Spirocyclization of Arylidene-Δ2-Pyrrolin-4-Ones with 3-Isothiocyanato Oxindoles

et al. 2020

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Arilidene-Δ2-pyrrolin-4-ones undergo organocatalyzed double spirocyclization with 3-isothiocianato oxindoles in a domino 1,4/1,2-addition sequence. The products contain three contiguous stereocenters (ee up to 98%, dr up to 99:1, 12 examples). The absolute configuration of the major diastereomer was determined by single crystal X-ray analysis. Along with heterocyclic Michael acceptors based on oxazolone, isoxazolone, thiazolidinone, pyrazolone, and pyrimidinedione, the reported results display the applicability of unsaturated Δ2-pyrrolin-4-ones (pyrrolones) for the organocatalyzed construction of 3D-rich pyrrolone-containing heterocycles.

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Construction of Spirocyclic Oxindoles through Regio‐ and Stereoselective [3+2] or [3+2]/[4+2] Cascade Reaction of α,β‐Unsaturated Imines with 3‐Isothiocyanato Oxindole

Cited by 36 publications

References 111 publications

Recent Advances in [3+2]-Cycloaddition-Enabled Cascade Reactions: Application to Synthesize Complex Organic Frameworks

Recent Advances in [3+2]-Cycloaddition-Enabled Cascade Reactions: Application to Synthesize Complex Organic Frameworks

Step Economy in the Stereoselective Synthesis of Functionalized Oxindoles via Organocatalytic Domino/One-pot Reactions

Double Spirocyclization of Arylidene-Δ2-Pyrrolin-4-Ones with 3-Isothiocyanato Oxindoles

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