Regiospecific and stereoselective synthesis of (1E,3Z )-3-cyano-butadienylphosphonates
- 1 January 1999
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 3495-3498
- https://doi.org/10.1039/a905941e
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.Keywords
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