N-Alkylation and [2,3]-sigmatropic rearrangement of N-allyl α-amino esters

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

Iain Coldham, Mark L. Middleton and Philip L. Taylor


Abstract

N-Alkylation of N-allyl α-amino esters and [2,3]-Stevens rearrangement occur in one pot on warming in the solvent DMF, with the bases K2CO3 and DBU; this in situ formation of the quaternary ammonium salts and rearrangement of the subsequent ylides gives N,N-dialkylated allyl glycine derivatives.


References

  1. I. Coldham, J. Chem. Soc., Perkin Trans. 1, 1993, 1275 RSC; I. Coldham, A. J. Collis, R. J. Mould and R. E. Rathmell, J. Chem. Soc., Perkin Trans. 1, 1995, 2739 RSC.
  2. For other examples of the aza-Wittig rearrangement, see Y. Murata and T. Nakai, Chem. Lett., 1990, 2069 Search PubMed; J. C. Anderson, D. C. Siddons, S. C. Smith and M. E. Swarbrick, J. Chem. Soc., Chem. Commun., 1995, 1835 CAS; R. E. Gawley, Q. Zhang and S. Campagna, J. Am. Chem. Soc., 1995, 117, 11817 RSC; S. V. Kessar, P. Singh, K. N. Singh, V. K. Kaul and G. Kumar, Tetrahedron Lett., 1995, 36, 8481 CrossRef CAS; J. Åhman, T. Jarevång and P. Somfai, J. Org. Chem., 1996, 61, 8148 CrossRef CAS.
  3. J. C. Anderson, D. C. Siddons, S. C. Smith and M. E. Swarbrick, J. Org. Chem., 1996, 61, 4820 CrossRef CAS; C. Vogel, Synthesis, 1997, 497 CrossRef CAS.
  4. I. E. Markó, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, 1991, vol. 3, ch. 3.10 Search PubMed; R. Brückner, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming, Pergamon Press, 1991, vol. 6, ch. 4.6 Search PubMed; I. Coldham, in Comprehensive Organic Functional Group Transformations, ed. A. R. Katritzky, O. Meth-Cohn and C. W. Rees, Pergamon Press, 1995, vol. 1, ch. 1.09 Search PubMed.
  5. S. T. Kocharyan, S. M. Ogandzhanyan and A. T. Babayan, Arm. Khim. Zh., 1976, 29, 42 Search PubMed; E. Vedejs, M. J. Arco and J. M. Renga, Tetrahedron Lett., 1978, 523 CrossRef CAS; R. M. Jemison, T. Laird, W. D. Ollis and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1980, 1450 RSC; S. Mageswaran, W. D. Ollis and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1981, 1953 RSC.
  6. W. D. Ollis, I. O. Sutherland and Y. Thebtaranonth, J. Chem. Soc., Perkin Trans. 1, 1981, 1963 RSC; S. J. Neeson and P. J. Stevenson, Tetrahedron Lett., 1988, 29, 3993 CrossRef CAS; K. Honda, S. Inoue and K. Sato, J. Am. Chem. Soc., 1990, 112, 1999 CrossRef CAS; K. Honda, S. Inoue and K. Sato, J. Org. Chem., 1992, 57, 428 CrossRef CAS; T. S. Bailey, J. B. Bremner and J. A. Carver, Tetrahedron Lett., 1993, 34, 3331 CrossRef CAS; K. Honda, M. Tabuchi and S. Inoue, Chem. Lett., 1996, 385 CAS; M. Gulea-Purcarescu, E. About-Jaudet, N. Collignon, M. Saquet and S. Masson, Tetrahedron, 1996, 52, 2075 CrossRef CAS.
  7. M. P. Doyle, W. H. Tamblyn and V. Bagheri, J. Org. Chem., 1981, 46, 5094 CrossRef CAS; J. S. Clark and P. B. Hodgson, Tetrahedron Lett., 1995, 36, 2519 CrossRef CAS; J. S. Clark and P. B. Hodgson, J. Chem. Soc., Chem. Commun., 1994, 2701 RSC; D. L. Wright, R. M. Weekly, R. Groff and M. C. McMills, Tetrahedron Lett., 1996, 37, 2165 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.