( E )-Selective Synthesis of γ-Substituted-β-(Ethoxycarbonyl)Allylsilanes Utilising Ethyl 2-Diphenylphosphono-3-(Trimethylsilyl)Propionate. Improved Synthesis of 11 Membered Carbocycle by a Homo-Cope Reaction †
( E )-Selective Synthesis of γ-Substituted-β-(Ethoxycarbonyl)Allylsilanes Utilising Ethyl 2-Diphenylphosphono-3-(Trimethylsilyl)Propionate. Improved Synthesis of 11 Membered Carbocycle by a Homo-Cope Reaction †
(E)-γ-Substituted-β-(ethoxycarbonyl)allylsilanes were selectively synthesised by Horner-Wadsworth-Emmons reaction utilising ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate.
For examples: (a) KurodaC., Recent Res. Devel. Pure Appl. Chem., 1998, 2, 189; (b) C. Kuroda, N. Mitsumata and C. Y. Tang, Bull. Chem. Soc. Jpn., 1996, 69, 1409; (c) C. Kuroda, C. Y. Tang, M. Tanabe and M. Funakoshi, Bull. Chem. Soc. Jpn., 1999, 72, 1583; (d) C. Kuroda and H. Koshio, Chem. Lett., 2000, 962; (e) C. Kuroda, K. Kobayashi, A. Koito and S. Anzai, Bull. Chem. Soc. Jpn., 2001, 74, 1947.
2.
Reviews for the reaction of allylsilanes: (a) LangkopfE., and SchinzerD., Chem. Rev.1995, 95, 1375; (b) I. Fleming, A. Barbero and D. Walter, Chem. Rev. 1997, 97, 2063.
3.
SuzukiH., MondaA., and KurodaC., Tetrahedron Lett., 2001, 42, 1915.
4.
(a) PornetJ., KhouzB., and MiginiacL., Tetrahedron Lett., 1985, 26, 1861; (b) J. Pornet, A. Rayadh and L. Miginiac, Tetrahedron Lett., 1986, 27, 5479; (c) J. Pornet, A. Rayadh and L. Miginiac, Tetrahedron Lett., 1986, 27, 4717.
5.
(a) NishitaniK., and YamakawaK., Tetrahedron Lett., 1987, 28, 655; (b) K. Nishitani, Y. Nakamura, R. Orii, C. Arai and K. Yamakawa, Chem. Pharm. Bull., 1993, 41, 822.
6.
HenningR., and HoffmannH. M. R., Tetrahedron Lett., 1982, 23, 2305.
7.
(a) AndoK., Tetrahedron Lett., 1995, 36, 4105; (b) K. Ando, J. Org. Chem. 1997, 62, 1934; (c) K. Ando, J. Org. Chem. 1998, 63, 8411; (d) K. Ando, J. Org. Chem. 1999, 64, 8406.
