DBU‐Catalyzed Ring‐Opening and Retro‐Claisen Fragmentation of Dihydropyranones §

We present a general protocol for the formal Michael addition of acetone to α,β‐unsaturated esters and amides, a transformation difficult to perform using current methods. The protocol comprises of an amidine catalyzed relay ring‐opening and fragmentation of 3,4‐dihydropyranones. The reaction proceeds under mild conditions, has a broad substrate scope and the products can be isolated in good to excellent yields. The method can be applied to homochiral substrates with total preservation of chiral information, generating products in high optical purity. Kinetic experiments supported by quantum chemical modeling indicate a mechanism in which the catalyst takes a bifunctional role, acting both as a Brønsted base and as a hydrogen‐bond donor.

Angaben zum Objekt

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

Verweise und Beziehungen

• Erschienen in: DBU‐Catalyzed Ring‐Opening and Retro‐Claisen Fragmentation of Dihydropyranones § ; volume:2020 ; number:33 ; year:2020 ; pages:5436-5444 ; extent:9 ; European journal of organic chemistry ; 2020, Heft 33 (2020), 5436-5444 (gesamt 9)

Beteiligte, Orts- und Zeitangaben

• Urheber: Axelsson, Anton ; Hammarvid, Emmelie ; Rahm, Martin ; Sundén, Henrik

Weitere Informationen

• DOI: 10.1002/ejoc.202000858
• URN: urn:nbn:de:101:1-2022062809082737692186
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 15.08.2025, 07:33 MESZ