Inverse‐Electron‐Demand Diels‒Alder Reactions of 2‐Pyrones: Bridged Lactones and Beyond
| Autor: | Cyrille Kouklovsky, Aurélien de la Torre, Guanghao Huang |
|---|---|
| Přispěvatelé: | Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Bicyclic molecule
010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Total synthesis General Chemistry [CHIM.CATA]Chemical Sciences/Catalysis 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences 3. Good health chemistry.chemical_compound chemistry 2-Pyrone Electrophile Diels alder Organic chemistry ComputingMilieux_MISCELLANEOUS Diels–Alder reaction |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2020, ⟨10.1002/chem.202003980⟩ Chemistry-A European Journal, Wiley-VCH Verlag, In press, ⟨10.1002/chem.202003980⟩ |
| ISSN: | 0947-6539 1521-3765 |
| DOI: | 10.1002/chem.202003980⟩ |
| Popis: | International audience; Inverse‐electron‐demande Diels‐Alder (IEDDA) reactions of electron‐poor 2‐pyrones as electrophilic dienes have been extensively studied in the past fifty years. These reactions provide and efficient access to bridged bicyclic lactones and their derivatives, such as densely functionalized 1,3‐cyclohexadienes after CO 2 extrusion and polysubstituted aromatic compounds through elimination. This reaction has been used for the synthesis of many biologically active natural products and drug candidates. In this review, the developments of these IEDDA reactions including non‐catalytic, Lewis acid‐catalyzed and organocatalytic IEDDA reactions, and their applications in total synthesis are discussed in detail. |
| Databáze: | OpenAIRE |
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