Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes
A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly p...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/179831 |
| Acceso en línea: | http://hdl.handle.net/10261/179831 |
| Access Level: | acceso abierto |
| Palabra clave: | Oxepenes Synthesis |
| Sumario: | A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly productive process is the result of a cascade of three chemical events with the concomitant formation of a C-O bond, a C-C bond, and a endocyclic double bond, through a Prins cyclization followed by a Peterson-type elimination. This tandem reaction is chemoselective vs the classical Prins cyclization. |
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