View PDF Version
 
DOI: 10.1039/A703166A (Paper) Reference Section for: J. Chem. Res. (S), 1997, 394-395

Intermolecular Diastereoselective Nitrile Oxide Addition with Propargylic Ethers

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

Subramanian Baskaran, Chitra Baskaran and Girish K. Trivedi

Abstract

Cycloaddition reactions of the nitrile oxide 2 are performed with simple and stereogenic propargylic ethers 3–5, 7 and 11 in moderately high yield and with considerable regioselectivity.

References

  1. C. J. Easton, C. M. M. Hughes, G. P. Savage and G. W. Simpson, Adv. Heterocycl. Chem., 1994, 60, 261 Search PubMed and references cited therein.
  2. S. Hariharan and G. K. Trivedi, Indian J. Chem., 1988, 27, 994 Search PubMed; J. Vasu, P. J. Nadkarni, G. K. Trivedi and A. Steigel, Magn. Reson. Chem., 1991, 29, 645 Search PubMed; S. Baskaran and G. K. Trivedi, J. Chem. Res., 1995, (S) 308; (M) 1853 Search PubMed; 1996, (S)542; S. Baskaran, J. Vasu, K. K. Ram Prasad, G. K. Trivedi and J. Chandrasekhar, Tetrahedron, 1996, 52, 4515 Search PubMed; S. Baskaran, C. Baskaran, P. J. Nadkarni, G. K. Trivedi and J. Chandrasekhar, Tetrahedron, 1997, 53, 7057 Search PubMed.
  3. K. N. Houk, S. R. Moses, Y. D. Wu, N. G. Rondan, J. Vager, R. Schohe and F. R. Fronczek, J. Am. Chem. Soc., 1984, 106, 3880 Search PubMed.
  4. A. P. Kozilkowski and A. K. Ghosh, J. Org. Chem., 1984, 49, 2762 Search PubMed.
  5. J. Blad, J. C. Carretero and E. Dominguez, Tetrahedron: Asymmetry, 1995, 1035 Search PubMed and references cited therein.
  6. A. Padwa, U. Chiacchio, D. C. Dean, A. M. Schoffstall, A. Hassner and K. S. K. Murthy, Tetrahedron Lett., 1988, 29, 4169 Search PubMed.
  7. S. F. Matin and B. Dupre, Tetrahedron Lett., 1983, 24, 337 Search PubMed.
  8. C. D. Hurd, M. E. Nilson and D. M. Wiccholm, J. Am. Chem. Soc., 1950, 72, 4697 Search PubMed.
  9. A. J. Blake, E. C. Boyd, R. O. Gould and R. M. Paton, J. Chem. Soc., Perkin Trans. 1, 1994, 2841 Search PubMed.
  10. G. Mouzin, H. Cousse, J. P. Rieu and A. Duflos, Synthesis, 1983, 117 Search PubMed.
  11. For intra-cycloaddition see K. M. Short and K. B. Ziegler, Tetrahedron Let., 1993, 34, 75 Search PubMed.
  12. E. C. Boyd and R. M. Paton, Tetrahedron Lett., 1993, 34, 3169 Search PubMed.
  13. M. Mancera, I. Roffe and J. A. Galbis, Tetrahedron, 1995, 51, 6349 Search PubMed.