Generation of silyl group stabilized amide homoenolates by utilizing the complex-induced proximity effect (CIPE)

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Tsuyoshi Shinozuka, Tomoko Utsumi, Miharu Inagaki and Morio Asaoka


Abstract

Generation of silyl group stabilized amide homoenolates from 3-trimethylsilyl- and 3-dimethylphenyl-propanamide with BusLi–TMEDA at –78 °C and their reactions with chlorosilanes, diphenyldisulfide and alkyl halides were carried out.


References

  1. T. Houkawa, T. Ueda, S. Sakami, M. Asaoka and H. Takei, Tetrahedron Lett., 1996, 37, 1045 CrossRef CAS; M. Asaoka, M. Tanaka, T. Houkawa, T. Ueda, S. Sakami and H. Takei, Tetrahedron, 1998, 54, 471 CrossRef CAS.
  2. E. W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, London, 1988, ch. 1 Search PubMed; E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, ch. 4 Search PubMed; W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983, ch. 6 Search PubMed; I. Fleming, Comprehensive Organic Chemistry, ed. D. N. Jones, Pergamon Press, Oxford, 1979, vol. 3, part 13 Search PubMed.
  3. P. Beak and A. I. Meyers, Acc. Chem. Res., 1986, 19, 356 CrossRef CAS; P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552 CrossRef CAS; V. Snieckus, Chem. Rev., 1990, 90, 879 CrossRef CAS; D. J. Pippel, M. D. Curtis, H. Du and P. Beak, J. Org. Chem., 1998, 63, 2 CrossRef CAS.
  4. I. Fleming and D. A. Perry, Tetrahedron, 1981, 37, 4027 CrossRef CAS; M. Asaoka, T. Aida, S. Sonoda and H. Takei, Tetrahedron Lett., 1989, 30, 7075 CrossRef CAS; M. Asaoka, M. Sakurai and H. Takei, Tetrahedron Lett., 1991, 32, 7567 CrossRef CAS.
  5. I. Fleming, Chemtracts: Org. Chem., 1996, 9, 1 Search PubMed.
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