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.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
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)

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

DOI
10.1002/ajoc.202300193
URN
urn:nbn:de:101:1-2023061515114175341303
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
14.08.2025, 10:58 MESZ

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Beteiligte

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

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