Artículos de revistas
Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates
Fecha
2014-04Registro en:
Rodriguez, Juan Bautista; Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates; Georg Thieme Verlag Kg; Synthesis-stuttgart; 46; 9; 4-2014; 1129-1142
0039-7881
CONICET Digital
CONICET
Autor
Rodriguez, Juan Bautista
Resumen
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.