Metal-Catalyzed Cycloetherification Reactions of β,y- and y,δ-Allendiols: Chemo-, Regio-, and Stereocontrol in the Synthesis of Oxacycles
[EN]: Versatile routes that lead to a variety of functionalized enantiopure tetrahydrofurans, dihydropyrans, and tetrahydrooxepines are based on chemo-, regio-, and stereocontrolled metal-catalyzed oxycyclization reactions of β,- and ,δ-allendiols, which were readily prepared from (R)-2,3-O-isopropy...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2010 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/29533 |
| Acceso en línea: | http://hdl.handle.net/10261/29533 |
| Access Level: | acceso abierto |
| Palabra clave: | Allenes Cyclization Gold Palladium Platinum |
| Sumario: | [EN]: Versatile routes that lead to a variety of functionalized enantiopure tetrahydrofurans, dihydropyrans, and tetrahydrooxepines are based on chemo-, regio-, and stereocontrolled metal-catalyzed oxycyclization reactions of β,- and ,δ-allendiols, which were readily prepared from (R)-2,3-O-isopropylideneglyceraldehyde. The application of PdII, PtII, AuIII, or LaIII salts as the catalysts gives controlled access to differently sized oxacycles in enantiopure form. Usually, chemoselective cyclization reactions occurred exclusively by attack of the secondary hydroxy group (except for the oxybromination of phenyl β,-allenic diols 3 b and 3 d) to an allenic carbon atom. Regio- and stereocontrol issues are mainly influenced by the nature of the metal catalysts and substituents. |
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