A Temporary Phosphorus Tether/Ring-Closing Metathesis Strategy to Functionalized 1,4-Diamines

Abstract

The synthesis of 1,4-diamines containing the (Z)-1,4-diaminobut-2-ene subunit via a temporary phosphorus tether/RCM strategy is described. We have developed a new method utilizing phosphorus nuclei as suitable temporary tethers for the coupling of nonracemic allylic amines. This approach allows for the generation of C(2)-symmetric and unsymmetric 1,4-diamines 1-3, which may have considerable synthetic and biological utility. This represents the first synthetic pathway for the expedient coupling of two amines via a temporary tether approach. [structure: see text]