In-Catalyzed Regioselective [3+2] Cycloaddition of Alkenes with α,β-Unsaturated Keto-Carboxylic Acid Derivatives for
Somnath Ghosh1, Nirmala Mohanta1, Mallika Swaminathan1
1Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.
Abstract:
Herein, we report In(OTf)3-catalyzed activation of α,β-unsaturated keto-carboxylic acid/ester and successive regioselective (3+2) cycloaddition with alkene to afford diverse new γ-butyrolactone derivatives in very good yields. This expedient strategy is also applicable to α,β-unsaturated amido ester to form various C3-butyrolactone-substituted oxindole derivatives in very good yields. Mechanistic studies reveal initial activation of the ketone functionality by an In catalyst as the key role to obtain the regioselectivity.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Base-Catalyzed Aldol Addition Reaction
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
