A temporary phosphorus tether/ring-closing metathesis strategy to functionalized 1,4-diamines.
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]
Sprott
K T
KT
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.
McReynolds
M D
MD
Hanson
P R
PR
D003959:Diamines / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*
D003959:Diamines; D010758:Phosphorus