Palladium(ii)-catalyzed C3-allylation of 3-ethynyl-3-OBoc oxindole derivatives was achieved for the first time to access highly functionalized 3-allyl-3-ethynyl substituted oxindole derivatives for a broad range of substrates in very good yields (up to 94%). The synthetic applications of the allylated products were explored by synthesizing five and six membered carbocyclic spirooxindoles in moderate to very good diastereoselectivities. © The Royal Society of Chemistry.

Venkitasamy Kesavan

Department Of Biotechnology

Nandarapu Kumarswamyreddy

Muthuraj Prakash

Samydurai Jayakumar

Allylation

catalysis

Diastereoselectivities

Functionalized

Synthetic application

Palladium compounds

Fulltext

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

RSC Advances

3-Alkynyl-3-OBoc oxindoles underwent Cu(II) mediated Friedel-Crafts alkylation with indoles and phenols to yield of structurally diverse 3-alkynyl-3-indole/phenol-oxindole derivatives. The synthetic application of alkylated phenol derivatives were further demonstrated to biologically important new class of chromene fused spirooxindoles through intramolecular metal-free iodocyclization under mild reaction conditions with broad substrate scope in very good yields. © 2018 Elsevier Ltd

Tetrahedron Letters

Efficient synthesis of highly functionalized indole and phenol containing 3,3′-disubstituted oxindoles and chromene fused spirooxindoles

The synthesis of highly functionalized spirocarbocyclic oxindoles was accomplished for the first time, using a Hauser annulation strategy. A reaction between methyleneindolinones and arylsulfonylphthalides catalyzed by cesium carbonate gave access to a new class of biologically important spiro[indoline-3,2′-naphthalene] derivatives in very good yields. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

European Journal of Organic Chemistry

Efficient Synthesis of Highly Functionalized Spirocarbocyclic Oxindoles through Hauser Annulation

3-Alkynyl-3-OBoc (Boc = tert-butoxycarbonyl) oxindole derivatives underwent a CuII-mediated stereo- and regioselective Friedel–Crafts alkylation/5-exo-dig-cyclization with 2-naphthols or cyclic 1,3-diketones. This gave spirooxindole [2,1-b]furan motifs in good to excellent yields under ambient conditions, and the process has a wide substrate scope. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Stereoselective and Regioselective Assembly of Spirooxindole [2,1-b]furan Motifs through a Tandem Friedel–Crafts Alkylation/5-exo-dig-Cyclization

A new synthetic strategy to construct spirooxindole-naphthopyran scaffold has been demonstrated via Friedel-Crafts type/hemiketalization of oxindole α-ketoester with 2-naphthol. Under the established reaction condition, quaternary chiral center at C3-position of oxindole has been created with very good asymmetric induction up to 98 % for a broad range of substrates. DFT calculations, which account for the stereochemical outcome, were performed. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

ChemCatChem

Organocatalytic Enantioselective Assembly of Spirooxindole-naphthopyrans through Tandem Friedel-Crafts Type/Hemiketalization

A new bifunctional squaramide organocatalyst derived from l-proline mediated the first enantioselective synthesis of dihydrospiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives in excellent enantioselectivity by reacting pyrazolones with isatylidine β,γ-unsaturated α-ketoester. This new catalyst outperformed widely used thioureas and squaramides in inducing enantioselectivity. © 2016 American Chemical Society.

Organic Letters

Enantioselective Synthesis of Dihydrospiro[indoline-3,4′-pyrano[2,3-c]pyrazole] Derivatives via Michael/Hemiketalization Reaction

Advanced Synthesis & Catalysis

Palladium-Catalyzed Direct α-Arylation of Benzyl Thioethers with Aryl Bromides

Natural Product Reports

Simple indole alkaloids and those with a non-rearranged monoterpenoid unit

Organic & Biomolecular Chemistry

Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: synthesis of 2-oxindoles with all-carbon quaternary center

Chemistry - A European Journal

Protonation-Triggered Generation of Acylcobalt Species from Alkyne-[Co2(CO)6] Complexes and Their Reaction with Alkenes

Synlett

Nucleophilic Substitution of Secondary Alkyl-Substituted Propargyl Acetates: An Economic and Practical Indium Trichloride Catalyzed Access

Assembly of 3-allyl-3-ethynyl-oxindole motifs via palladium(ii)-catalyzed quaternary allylation of 3-ethynyl-3-OBoc-oxindoles

Journal	Data powered by TypesetRSC Advances
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	20462069
Open Access	No