Synthesis of vinyl epoxides via a three-component coupling

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

Martin W. Rowbottom, Neil Mathews and Timothy Gallagher


Abstract

The butadienylsulfonium species 1 undergoes stepwise addition of a stabilised enolate followed by trapping of the initially formed S-ylid 2 with an aldehyde to provide vinyl epoxides 3 in a two-step, three-component process.


References

  1. For leading references to the applications/reactivity of vinyl epoxides, see: B. M. Trost, Angew. Chem., Int. Ed. Engl., 1989, 28, 1173 Search PubMed; J. A. Marshall, Chem. Rev., 1989, 89, 1503 CrossRef; T. Hudlicky and J. W. Reed, in Comprehensive Organic Synthesis, eds. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, p. 899 CrossRef CAS; S. V. Ley, Pure Appl. Chem., 1994, 66, 1415 CrossRef CAS For more recent applications, see A. S. Batsanov, A. L. J. Byerley, J. A. K. Howard and P. G. Steel, Synlett, 1996, 401 Search PubMed; C. Larksarp and H. Alper, J. Am. Chem. Soc., 1997, 119, 3709 CAS; U. M. Lindstrom, R. Franckowiak, N. Pinault and P. Somfai, Tetrahedron Lett., 1997, 38, 2027 Search PubMed; J. Shim and Y. Yamamoto, J. Org. Chem., 1998, 63, 3067 CrossRef CAS; U. M. Lindstrom and P. Somfai, Synthesis, 1998, 109 CrossRef CAS.
  2. Epoxidation is widely used to prepare vinyl epoxides: M. Frohn, M. Dalkiewicz, Y. Tu, Z.-X. Wang and Y. Shi, J. Org. Chem., 1998, 63, 2948 Search PubMed and citations therein. Leading references to other preparative methods; (a) from glycidic esters: P. S. Vankar, I. Rhattacharya and Y. D. Vankar, Tetrahedron: Asymmetry, 1996, 7, 1683 Search PubMed; (b) from allyl S, Te and As salts: Z.-L. Zhou, Y.-S. Sun, L.-L. Shi and Y.-Z. Huang, Tetrahedron Lett., 1990, 31, 7657 Search PubMed; J. D. Hsi and M. Koreeda, J. Org. Chem., 1989, 54, 3229 CrossRef CAS; A. Osuka and H. Suzuki, Tetrahedron Lett., 1983, 24, 5109 CrossRef; J. B. Ousset, C. Mioskowski and G. Solladie, Tetrahedron Lett., 1983, 24, 4419 CrossRef CAS; M. J. Hatch, J. Org. Chem., 1969, 34, 2133 CrossRef CAS; R. W. LaRoochelle, B. M. Trost and L. Krepski, J. Org. Chem., 1971, 36, 1126 CrossRef CAS; (c) from chlorohydrins and related precursors: S. Jayaraman, S. Hu and A. C. Oehlschlager, Tetrahedron Lett., 1995, 36, 4765 Search PubMed; M. Julia, J. N. Verpeaux and T. Zahneisen, Bull. Soc. Chim. Fr., 1994, 539 CrossRef CAS; K. Mallaiah, J. Satyanarayana and H. Junjappa, Tetrahedron Lett., 1993, 34, 3145 CAS; (d) using other asymmetric oxidation methods: R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH Publishers, New York, 1993, pp. 103–158 Search PubMed.
  3. T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992 Search PubMed; R. A. Bunce, Tetrahedron, 1995, 51, 13103 Search PubMed; P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 1996, 96, 195 CrossRef CAS.
  4. H. Braun, N. Mayer and G. Kresze, Liebigs Ann. Chem., 1972, 111 Search PubMed; H. Braun, N. Mayer, G. Strobl and G. Kresze, Liebigs Ann. Chem., 1973, 1317 Search PubMed; H. Braun, G. Huber and G. Kresze, Tetrahedron Lett., 1973, 4033 CrossRef CAS.
  5. M. E. Garst, J. Org. Chem., 1979, 44, 1578 CrossRef CAS; M. E. Garst and P. Arrhenius, J. Org. Chem., 1983, 48, 16 CrossRef CAS.
  6. H. Braun and G. Huber, Tetrahedron Lett., 1976, 2121 CrossRef.
  7. D. A. Fletcher, R. F. McMeeking and D. J. Parkin, J. Chem. Inf. Comput. Sci., 1996, 36, 746 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.