Selective Vinylogous Aldol Reactions of β‐Methyl‐Substituted Cyclic Enones with Isatins Catalyzed by DBU and Pyrrolidine to Afford 3‐Substituted 3‐Hydroxyoxindoles

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Abstract: The development of regioselective aldol reactions of β‐methyl‐substituted cyclic enone derivatives with isatins to afford the aldol products with the bond formation at the methyl group of the β‐methyl‐substituted cyclic enone derivatives is described. Catalyst systems composed of DBU and pyrrolidine with DMSO were identified that resulted in the aldol reactions with almost perfect regioselectivities. DBU, pyrrolidine, and DMSO were all required to selectively afford the γ‐position‐reacted aldol products. With the use of this method, the scope of the 3‐substituted 3‐hydroxyoxindole derivatives that can be concisely synthesized was expanded.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Selective Vinylogous Aldol Reactions of β‐Methyl‐Substituted Cyclic Enones with Isatins Catalyzed by DBU and Pyrrolidine to Afford 3‐Substituted 3‐Hydroxyoxindoles ; day:14 ; month:06 ; year:2023 ; extent:7
Asian journal of organic chemistry ; (14.06.2023) (gesamt 7)

Creator: Bethi, Venkati
Zahra, Syeda Bakhtawar
Rupanawar, Bapuaro D.
Tanaka, Fujie

DOI: 10.1002/ajoc.202300193

URN: urn:nbn:de:101:1-2023061515114175341303

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:58 AM CEST

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Bethi, Venkati
Zahra, Syeda Bakhtawar
Rupanawar, Bapuaro D.
Tanaka, Fujie

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Selective Vinylogous Aldol Reactions of β‐Methyl‐Substituted Cyclic Enones with Isatins Catalyzed by DBU and Pyrrolidine to Afford 3‐Substituted 3‐Hydroxyoxindoles

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Other Objects (12)

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Direct Regioselective Dehydrogenation of α‐Substituted Cyclic Ketones

Zeolite catalyzed dehydration of substituted cyclic alcohols in aqueous phase

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Trifluoromethyl-substituted tetrathiafulvalenes

Substituted Cyclopentannulated Tetraazapentacenes

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Thermochemistry of substituted benzenes: acetophenones with methyl, ethyl, cyano and acetoxy substituents

Photooxygenation of substituted cycloheptatrienes

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Direct Regioselective Dehydrogenation of α‐Substituted Cyclic Ketones

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Neighboring-Group Effect: DBU-Promoted Ring Transformation of Substituted Isoxazoles to Substituted Pyrroles

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