Brønsted‐Acid Catalyzed Diastereo‐ and Enantioselective Synthesis of Spiroisoindolinones from Enamides

Abstract: A highly stereoselective Brønsted‐acid catalyzed synthesis of densely substituted spiroisoindolinones from enamides and 3‐hydroxy‐isoindolinones is described. With simple Brønsted‐acids, such as para‐toluene sulfonic acid, spiroisoindolinones with three contiguous stereogenic centers are formed in high yields (up to 97 %) and diastereoselectivities (up to >98: <2: 0: 0 dr) under mild reaction conditions. With the use of a chiral phosphoric acid catalyst, a diastereo‐ and enantioselective synthesis of the corresponding spiroisoindolinones was achieved. Mechanistic investigations indicate a step‐wise mechanism via an initial addition of the enamide to an electrophilic N‐acylimine species followed by an intramolecular aza‐Friedel‐Crafts reaction. Addition of a strong Lewis acid can be used to facilitate the second step for less reactive substrates.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Brønsted‐Acid Catalyzed Diastereo‐ and Enantioselective Synthesis of Spiroisoindolinones from Enamides ; day:11 ; month:12 ; year:2024 ; extent:11 ; Chemistry - a European journal ; (11.12.2024) (gesamt 11)

Contributors, Places and Time

• Creator: Halaczkiewicz, Miro ; Maraj, Arianit ; Riedel, Mareike ; Donner, Leon ; Kelm, Harald ; Manolikakes, Georg

Further information

• DOI: 10.1002/chem.202404223
• URN: urn:nbn:de:101:1-2412121317288.418505016343
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:27 AM CEST