Molecular Iodine-Mediated Ring Opening Reaction of Spiro-Epoxy Oxindoles with Electron Rich Arenes

Catalytic asymmetric C3-indolylation of N-protected spiro-epoxyoxindoles has been developed for the access of 3-(3-indolyl)-oxindole methanols with excellent enantioselectivity (ee up to > 99%). The widespread substrate scope and easily accessible Co(III)-salen over 1,1'-Spirobiindane-7,7'-diol phosphoric acid prove our condition to be more beneficial than the chiral Brønsted acid-catalyzed reaction. Further, kinetic resolution of spiro-epoxides is achieved in high enantiomeric excess under certain conditions. The detailed mechanistic study endorses that the feedback inhibition played a key role which restricts the dynamic kinetic resolution process. Besides it also revealed the S N 2' mechanism for the Co(III)-salen catalysed C3-indolylation of spiro-epoxyoxindoles.

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Co(III)salen Catalyzed Enantioselective C3‐Indolylation of Spiro‐Epoxyoxindoles and Its Mechanistic Studies

Hajra

Roy

Mondal

2020

Adv Synth Catal

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Regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles

Bao

Zhu

et al. 2018

Org. Biomol. Chem.

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A highly efficient strategy for the regio- and stereospecific Friedel-Crafts alkylation of indoles with spiro-epoxyoxindoles has been developed in the mixed solvents of HFIP/H2O (1 : 9) without the use of catalysts. This protocol provides an atomically economical, catalyst-free and simple route for the construction of synthetically useful 3-(3-indolyl)-oxindole-3-methanols in high yields. Starting from optically active spiro-epoxyoxindoles a variety of enantiospecific 3-(3-indolyl)-oxindole-3-methanols could be obtained in high yields with complete retention of enantioselectivity.

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Synthesis and Anticancer Activity of a Novel Series of Tetrazolo[1,5-a]quinoline Based 1,2,3-Triazole Derivatives

et al. 2020

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Molecular Iodine-Mediated Ring Opening Reaction of Spiro-Epoxy Oxindoles with Electron Rich Arenes

Cited by 3 publications

References 38 publications

Co(III)salen Catalyzed Enantioselective C3‐Indolylation of Spiro‐Epoxyoxindoles and Its Mechanistic Studies

Co(III)salen Catalyzed Enantioselective C3‐Indolylation of Spiro‐Epoxyoxindoles and Its Mechanistic Studies

Regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles

Synthesis and Anticancer Activity of a Novel Series of Tetrazolo[1,5-a]quinoline Based 1,2,3-Triazole Derivatives

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