Dihydropyrans by Cycloadditions of Oxadienes
| Autor: | Catherine Gaulon, Arnaud Martel, Gilles Dujardin, Mathieu Y. Laurent, Robert Dhal |
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| Přispěvatelé: | Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), P. Andrew Evans |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Hetero‐Diels-Alder
010405 organic chemistry Chemistry Dihydropyran [CHIM.ORGA]Chemical Sciences/Organic chemistry Single step 010402 general chemistry 01 natural sciences Combinatorial chemistry Inverse‐electron‐demand Cycloaddition 0104 chemical sciences Stereocenter Catalysis chemistry.chemical_compound [CHIM]Chemical Sciences Lewis acids and bases Oxadiene Catalyst |
| Zdroj: | P. Andrew Evans. Wiley, 101, pp.1-550, 2020, Organic Reactions, ⟨10.1002/0471264180.or101.01⟩ Organic Reactions |
| DOI: | 10.1002/0471264180.or101.01⟩ |
| Popis: | International audience; 3,4‐Dihydro‐2H‐pyrans are present in the skeletons of several natural products, and these versatile synthetic intermediates are readily transformed into tetrahydropyrans, pyridines, or 1,5‐dicarbonyl units. Among the strategies developed to access 3,4‐dihydro‐2H‐pyrans, the hetero‐Diels‐Alder reaction between an oxadiene and a dienophile is particularly valuable because up to three contiguous stereogenic centers can be created diastereo‐ and/or enantioselectively in a single step. This review addresses the mechanism of the reaction and presents methods for preparing the product dihydropyrans enantio‐ and diastereoselectively. Thermal and Lewis acid promoted cycloadditions are discussed, as is the role of activating groups on the oxadiene. |
| Databáze: | OpenAIRE |
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