The radical hydrostannation of 1-alkynylphosphonates gives the (Z)-α-stannyl-1-alkenylphosphonates 2 stereoselectively; 2 can be transformed into α-iodo-1-alkenylphosphonates and α-substituted vinylphosphonates with retention of configuration.
(a) SonogashiraK., TohdaY., and HagiharaN., Tetrahedron Lett., 1975, 4467; (b) M. Alami and G. Linstrumelle, Tetrahedron Lett., 1991, 32, 6109; (c) M. Alami, J-F. Peyrat and J.-D. Brion, Synthesis., 2000, 1449; (d) W. J. Scott, M. R. Pena, K. Swand, S. J. Stoessel and J. K. Stick, J. Org. Chem., 1985, 50, 2302; (e) Z. Wang and K. K. Wang, J. Org. Chem., 1994, 59, 4738.
2.
As intermediates in drugs or biological investigation compounds. (a) HarndnM.R., ParratM. J., and PerkinR. M., J. Med. Chem., 1993, 36, 1343; (b) S. Magati, S. Phadtare and J. Zemlica, J. Org. Chem., 1992, 57, 2320.
3.
PereyneM., QuintardJ. P., and RahmA., Tin in Organic Synthesis.Butterworth, London. 1980.
4.
(a) SeyferthD., and WeinerM. A., J. Am. Chem. Soc., 1961, 83, 7585; (b) V. Farina and S. I. Hauck, J. Org. Chem., 1991, 56, 4317; (c) J. K. Stille, Angew. Chem Ed. Eng, 1986, 25, 508; (d) J. K. Stille, Pure Appl. Chem., 1985, 57, 1771; (e) W. J. Scott and J. K Stille, J. Am. Chem. Soc., 1986, 108, 3033.
5.
(a) KenyonG.L, and WestheimerF. H., J. Am. Chem. Soc., 1966, 88, 3557; (b) C. Benzra, S. Nseic and G. Ourisson, Bull. Soc. Chim. Fr., 1967, 1140
