Intramolecular alkylation of an α-sulfinyl vinylic carbanion without loss of optical purity: a novel access to chiral cyclic vinylic sulfoxides

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Naoyoshi Maezaki, Mayuko Izumi, Sachiko Yuyama, Chuzo Iwata and Tetsuaki Tanaka


Abstract

Novel cyclisation via intramolecular α-alkylation of vinylic sulfoxides was studied and cyclic vinylic sulfoxides of various ring sizes (5–7) were synthesised from both (E)- and (Z)-isomers without loss of optical purity.


References

  1. (a) R. R. Schmidt, H. Speer and B. Schmid, Tetrahedron Lett., 1979, 4277 CrossRef CAS; (b) G. H. Posner, P.-W. Tang and J. P. Mallamo, Tetrahedron Lett., 1978, 42, 3995 CrossRef; (c) H. Okamura, Y. Mitsuhira, M. Miura and H. Takei, Chem. Lett., 1978, 517 CAS.
  2. Review: M. C. Carreño, Chem. Rev., 1995, 95, 1717 Search PubMed.
  3. G. H. Posner, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 2A, pp. 225–241 Search PubMed; G. H. Posner, J. P. Mallamo and K. Mirua, J. Am. Chem. Soc., 1981, 103, 2886 Search PubMed.
  4. N. Maezaki, A. Sakamoto, T. Tanaka and C. Iwata, Tetrahedron: Asymmetry, 1998, 9, 179 CrossRef CAS; N. Maezaki, A. Sakamoto, M. Soejima, I. Sakamoto, Y.-X. Li, T. Tanaka, H. Ohishi, K. Sakaguchi and C. Iwata, Tetrahedron: Asymmetry, 1996, 7, 2787 CrossRef CAS and references cited therein.
  5. Concomitant isomerisation-alkylation of an α-sulfinyl carbanion on an sp3 carbon has been reported, see: G. Chassaing, R. Lett and A. Marquet, Tetrahedron Lett., 1978, 471 Search PubMed.
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