Stereoselective formation of (Z)-γ-substituted allylsilanes by the titanocene(II)-promoted reaction of thioacetals with trialkyl(allyl)silanes

(Note: The full text of this document is currently only available in the PDF Version )

Tooru Fujiwara, Mayumi Takamori and Takeshi Takeda


Abstract

The reaction of organotitanium species prepared by the desulfurizative titanation of thioacetals with (C5H5)2Ti[P(OEt)3]2 in the presence of trialkyl(allyl)silanes gives γ-substituted allylsilanes with Z stereoselectivity.


References

  1. D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104 CrossRef CAS ; D. Seyferth, K. R. Wursthorn and T. F. O. Lim, J. Organomet. Chem., 1979, 181, 293 CrossRef CAS ; I. Fleming and I. Paterson, Synthesis, 1979, 446 CrossRef CAS ; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112 CrossRef CAS .
  2. W. E. Crowe, D. R. Goldberg and Z. J. Zhang, Tetrahedron Lett., 1996, 37, 2117 CrossRef CAS  The molybdenum-catalysed cross metathesis of terminal olefins with allylstannanes has also been reported; J. Feng, M. Schuster and S. Blechert, Synlett, 1997, 129 Search PubMed .
  3. M. F. Schneider, N. Lucas, J. Velder and S. Belchert, Angew. Chem., Int. Ed. Engl., 1997, 36, 257 CrossRef CAS .
  4. Y. Horikawa, M. Watanabe, T. Fujiwara and T. Takeda, J. Am. Chem. Soc., 1997, 119, 1127 CrossRef CAS .
  5. Y. Horikawa, T. Nomura, M. Watanabe, T. Fujiwara and T. Takeda, J. Org. Chem., 1997, 62, 3678 CrossRef CAS .
  6. T. Takeda, H. Shimokawa, Y. Miyachi and T. Fujiwara, Chem. Commun., 1997, 1055 RSC .
  7. The regio- and stereo-selective formation of trans-α,β-disubstituted titanacyclobutanes by the reaction of trimethylsilylmethylene complex (C5Me5)2Ti[double bond, length as m-dash]CHSiMe3 with terminal olefins was reported; J. L. Polse, R. A. Andersen and R. G. Bergman, J. Am. Chem. Soc., 1996, 118, 8737 Search PubMed .
  8. J. R. Stille, B. D. Santarsiero and R. H. Grubbs, J. Org. Chem., 1990, 55, 843 CrossRef CAS .
  9. D. A. Straus and R. H. Grubbs, J. Mol. Catal., 1985, 28, 9 CrossRef CAS .
  10. S. Rajagopalan and G. Zweifel, Synthesis, 1984, 113 CrossRef CAS .
  11. A. Thalman, K. Oertle and H. Gerlach, Org. Synth., 1990, Coll. Vol. VII, 470 .
Click here to see how this site uses Cookies. View our privacy policy here.