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

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journal contribution
posted on 27.10.2001, 00:00 by Kevin T. Sprott, Matthew D. McReynolds, Paul R. Hanson
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 C2-symmetric and unsymmetric 1,4-diamines 13, 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.