Regiospecific and stereoselective synthesis of (1E,3Z )-3-cyano-butadienylphosphonates

Abstract

Treatment of a catalytic amount of DBU (20 mol%) with a mixture of diethyl 3-cyanoallylphosphonate 1 and N-tosylsulfonylimines 2 gave diethyl 3-cyanobuta-1,3-dienylphosphonates 3 in 72–83% yields. All the products (3a–3h) are assigned 1E,3Z configurations on the basis of the crystal structure of diethyl (1E,3Z )-3-cyano-4-naphthylbuta-1,3-dienylphosphonate (3h), the proton NMR spectra and the proposed reaction mechanism.

References

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