Topic
Oxindole
About: Oxindole is a research topic. Over the lifetime, 2146 publications have been published within this topic receiving 47668 citations. The topic is also known as: 2-oxindole & 1,3-dihydroindol-2-one.
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TL;DR: The spiro[pyrrolidine-3,3′-oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis as discussed by the authors.
1,267 citations
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TL;DR: 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.
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.
1,085 citations
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TL;DR: This review highlights the advances in the literature up to May2009 in the synthesis of spirocyclic indoline natural products, including bothenantioselective and diastereoselectives methods.
Abstract: This review highlights the advances in the literature up to May2009 in the synthesis of spirocyclic indoline natural products. Thefocus is on formation of the spirocyclic chiral center, including bothenantioselective and diastereoselective methods. This review issplit into two main sections, the first consisting of the formation ofspirooxindoles and their application towards oxindole alkaloids, andthe second covering asymmetric synthesis of spiroindoline naturalproducts. 1 Introduction 2 Spirooxindole Alkaloids 2.1 Oxidative Rearrangements 2.2 Azomethine Ylide Cycloaddition 2.3 Asymmetric Addition-Elimination 2.4 Palladium-Catalyzed Heck Reactions 2.5 Palladium-Catalyzed Allylic Alkylation 2.6 Ring Expansion 2.7 Mannich Reaction 3 Spiroindoline Alkaloids 3.1 Palladium Catalyzed Asymmetric Allylic Alkylation 3.2 [4+2] Cycloaddition 3.3 Oxidative Rearrangement 3.4 Diastereoselective Pummerer Rearrangement 3.5 Tandem Iminium Cascade 3.6 Fischer Indole Synthesis 3.6.1 Diastereoselective Ring-Closing Metathesis 3.6.2 Diastereoselective Alkylation of Chiral Lactams 3.6.3 Regioselective Schmidt Reaction 3.6.4 Diastereoselective Ketene Lactonization 3.6.5 Harley-Mason Reaction 3.6.6 S N 2-Type Indole Alkylation 3.6.7 Aza-Cope-Mannich Rearrangement 4 Conclusion
937 citations
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TL;DR: This Review focuses on the comparison of the different strategies to assemble the bicyclo[3.2.1]octane core, to introduce the bridgehead quaternary C20 to form the pyrrolidine moiety, to construct the oxindole residue, and to close the tetrahydropyran ring en route to gelsemine.
Abstract: Gelsemine and 21-oxogelsemine have been synthesized through several routes. This Review focuses on the comparison of the different strategies to assemble the bicyclo[3.2.1]octane core, to introduce the bridgehead quaternary C20 to form the pyrrolidine moiety, to construct the oxindole residue, and to close the tetrahydropyran ring en route to gelsemine.
529 citations
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TL;DR: Mechanistic studies showed that the reaction involves rate-limiting oxidative addition of aryl halide, and use of new, optically active heterocyclic carbene ligands gave substantial enantioselectivity in formation of an alpha,alpha-disubstituted oxindole.
Abstract: Catalysts comprised Pd(OAc)2 and either PCy3 or sterically hindered N-heterocyclic carbene ligands provide fast rates for a palladium-catalyzed synthesis of oxindoles by amide α-arylation. This catalyst system allowed for room-temperature reactions in some cases and reactions of aryl chlorides at 70 °C. Most important, reactions occurred in high yields under mild conditions to form the quaternary carbon in α,α-disubstituted oxindoles. The combined inter- and intramolecular reaction afforded an efficient synthetic method for formation of α-aryloxindole derivatives. Surprisingly, catalysts containing tert-butylphosphine ligands, which have been most reactive for ketone arylations, were less active than those containing PCy3. Use of new, optically active heterocyclic carbene ligands gave substantial enantioselectivity in formation of an α,α-disubstituted oxindole. In contrast, a variety of optically active phosphine ligands that were tested gave poor enantioselectivity. Mechanistic studies showed that the re...
483 citations