Intramolecular C-H Insertion Reactions of Boroxy Fischer Carbene Complexes. Regio and Diastereoselective Modification of Terpenes
In-situ-generated dialkylboroxy and diaminoboroxy Fischer carbene complexes lead to oxaborolane or oxazaborolidine derivatives via an intramolecular C-H insertion reaction. Further oxidation of these intermediates yields 1,3-diol or 1,2-amino alcohol derivatives. Diastereoselectivities as high as 99...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 1999 |
| País: | España |
| Institución: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc68e3b750603269e8115f |
| Acceso en línea: | https://investigacion.unirioja.es/documentos/5bbc68e3b750603269e8115f |
| Access Level: | acceso abierto |
| Sumario: | In-situ-generated dialkylboroxy and diaminoboroxy Fischer carbene complexes lead to oxaborolane or oxazaborolidine derivatives via an intramolecular C-H insertion reaction. Further oxidation of these intermediates yields 1,3-diol or 1,2-amino alcohol derivatives. Diastereoselectivities as high as 99% are reached when starting from boroxy Fischer carbene complexes derived from terpenes, which represents a regio- and diastereoselective modification of this type of natural product. The influence of the C(β) substituents relative to the boron atom on the reaction path is studied, and a mechanism is proposed after identification of an intermediate by NMR. In addition, theoretical calculations show the presence of a boron-metal interaction, which could result as key step to the C-H insertion reaction. |
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