Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including str...
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2014 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/18678 |
| Acceso en línea: | http://hdl.handle.net/11336/18678 |
| Access Level: | acceso abierto |
| Palabra clave: | Bisphosphonates Michael Addition 1,3-Dipolar Cycloaddition Diels-Alder Reaction https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels–Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action. |
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