A regio- and stereoselective synthesis of substituted allyl selenides is described. Hydrozirconation of propargyl selenides and its further reaction with aldehydes or acyl chlorides afford 4-selanyl allyl alcohols or 4-selanyl-2-en-1-one, respectively.
(a). CliveD.L. J., Tetrahedron, 1979, 34, 1049; (b). H. J. Reich, M. C. Clark, and W. W., Jr., Willis, J. Org. Chem. 1982, 47, 1618; (c) H. J. Reich, J. Org. Chem. 1975, 40, 2570.
2.
ReichH.J., [2, 3] Sigmatropic rearrangements of organoselenium compounds, in LiottaD. ed., Organoselenium Chemistry, John Wiley, New York (1987).
3.
TakeiH., MiuraM., KosugiK., and TakeiH., Tetrahedron Lett.1980, 21, 87.
4.
(a) HuangX., and XuX. H., Synth. Commun.1998, 28, 801; (b) S. Fukuzawa, T. Fujinami and S. Sakai, Chem. Lett., 1990, 6, 927.
5.
(a). SchwartzJ., J. Organomet. Chem., Library1976, 1, 461; (b). D. W. Hart, T. F. Blackburn, and J. Schwartz, J. Am. Chem. Soc. 1975, 97, 679.
6.
(a). Review: WipfP., and JahnH., Tetrahedron1996, 52, 12853; (b). M. J. Dabdoub, M. L. Begnini, and P. G. Jr Guerrero, Tetrahedron 1998, 54, 2371.
7.
(a). MaetaH., and SuzukiK., Tetrahedron Lett.1992, 33, 5969; (b). D. Orain, and J. C. Guillemin, J. Org. Chem. 1999, 64, 3563.
8.
(a). HuangX., and ZhuL. S., J. Organomet. Chem., 1996, 529, 9; (b) A. M. Sun and X. Huang, Tetrahedron 1999, 55, 13201; (c) A. M Sun and X. Huang, Synthesis 2000, 775.
9.
BrandsmaL., and VerkruijsseH. D., Synthesis of Acetylenes, Allenes and Cumulenes;Elsevier, New York, 1981, p. 235.
10.
HartD. W., and SchwartzJ., J. Am. Chem. Soc.1974, 96, 8115.