Ring-Opening Cyclization(ROC) of <i>spiro</i>-Epoxyoxindoles with Indoles/Aldehydes:An Easy Access to Polyheterocyclic <i>spiro</i>-Oxindoles

A simple one-pot, two-step strategy for the synthesis of three-dimensional (3D) polyheterocyclic <i>spiro</i>-oxindoles by Lewis-acid-catalyzed Friedel–Crafts type <i>C</i>-3 alkylation of indoles <i>via</i> regioselective nucleophilic ring opening of <i>spiro</i>-epoxyoxindoles, followed by <i>p</i>-TSA-catalyzed Pictet-Spengler reaction with aldehydes in up to 98% yield and 1.4:1 diastereomeric ratio has been developed.

Publication Details

Journal
Figshare
Published
2025-03-10
DOI
https://doi.org/10.1021/acs.joc.4c02906.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Ring-Opening Cyclization(ROC) of spiro-Epoxyoxindoles with Indoles/Aldehydes:An Easy Access to Polyheterocyclic spiro-Oxindoles

Figshare
Catalytic C–H Functionalization Methods
article

Ring-Opening Cyclization(ROC) of spiro-Epoxyoxindoles with Indoles/Aldehydes:An Easy Access to Polyheterocyclic spiro-Oxindoles

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Abstract

A simple one-pot, two-step strategy for the synthesis of three-dimensional (3D) polyheterocyclic <i>spiro</i>-oxindoles by Lewis-acid-catalyzed Friedel–Crafts type <i>C</i>-3 alkylation of indoles <i>via</i> regioselective nucleophilic ring opening of <i>spiro</i>-epoxyoxindoles, followed by <i>p</i>-TSA-catalyzed Pictet-Spengler reaction with aldehydes in up to 98% yield and 1.4:1 diastereomeric ratio has been developed.

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Catalytic C–H Functionalization Methods
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Ring-Opening Cyclization(ROC) of <i>spiro</i>-Epoxyoxindoles with Indoles/Aldehydes:An Easy Access to Polyheterocyclic <i>spiro</i>-Oxindoles · Figshare (2025) | TGRS Research Map | TGRS