Stannatrane (original) (raw)

A stannatrane (IUPAC: 1-aza-5-stannabicyclo[3.3.3]undecane) is a tin-based atrane belonging to the larger class of organostannanes. Though the term stannatrane is often used to refer to the more commonly employed carbastannatrane, azastannatranes have also been synthesized (prefix refers to the identity of the atom bound directly to tin center). Stannatrane reagents offer highly selective methods for the incorporation of "R" substituents in complex molecules for late-stage diversification. These reagents differ from their tetraalkyl organostannane analogues in that there is no participation of in the transmetalation step, offering selective in Stille Coupling reactions. These transmetalating agents are known to be air- and moisture-stable, as well as generally less toxic than their tetra