Stereoselectivity of intramolecular cyclisations of nitrones derived from 3-oxahept-6-enals

Abstract

Intramolecular [1,3]-dipolar cycloadditions of nitrones 33, derived from 3-oxahept-6-enals 7, substituted at either the 4- or 5-position and prepared using a variety of approaches, give good to excellent yields of the cycloadducts 34–37, with good levels of stereoselectivity, especially when the substituent is adjacent to the alkene. The cyclisations appear to proceed via well-defined transition state conformations which should be of predictive value.

References

1. P. Lefrancier, Forschr. Chem. Org. Naturst., 1981, 40, 1; E. Ellouz, A. Adam, R. Ciorbaru and E. Lederer, Biochem. Biophys. Res. Commun., 1974, 59, 1317.
2. M. A. Sparks, K. W. Williams, C. Lukacs, A. Schrell, G. Priebe, A. Spaltenstein and G. M. Whitesides, Tetrahedron, 1993, 49, 1; M. P. DeNinno, Synthesis, 1991, 583 and references cited therein.
3. P. M. Colman, Pure Appl. Chem., 1995, 67, 1683 and references cited therein.
4. T. Wakamiya, T. Ando, T. Teshima and T. Shiba, Bull. Chem. Soc. Jpn., 1984, 57, 142; Y. Hayakawa, M. Nakagawa, H. Kawai, K. Tanabe, H. Nakayama, A. Shimazu, H. Seto and H. Otake, Agric. Bio. Chem., 1985, 49, 2685.
5. F. M. Hauser and S. R. Ellenberger, Chem. Rev., 1986, 86, 35 and references cited therein.
6. J. J. Tufariello, [1,3]-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley Interscience, New York, 1984, ch. 9; P. A. Wade, Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, p. 1113; K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH Publishers Inc., Weinheim, 1988, ch. 5; W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990; E. Breuer, H. G. Aurich and A. Nielsen, Nitrones, Nitronates and Nitroxides, eds. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1989.
7. N. A. LeBel, M. E. Post and J. J. Whang, J. Am. Chem. Soc., 1964, 86, 3759; N. A. LeBel and E. G. Banucci, J. Org. Chem., 1971, 36, 2440.
8. B. Bernat and A. Vassella, Helv. Chim. Acta, 1979, 62, 2400 and 2411.
9. H. G. Aurich and K.-D. Möbus, Tetrahedron, 1989, 45, 5815; H. G. Aurich and F. Biesemeier, Synthesis, 1995, 1171; H. G. Aurich, F. Biesemeier and M. Boutahar, Chem. Ber., 1991, 124, 2329 See also S. Baskaran and H. G. Aurich, Synlett, 1998, 277; H. G. Aurich, G. Frenzen and C. Gentes, Chem. Ber., 1993, 126, 787.
10. H. G. Aurich, M. Geiger and U. Sievers, Synlett, 1997, 1004; H. G. Aurich, F. Biesemeier, M. Geiger and K. Harms, Liebigs Ann./Recl., 1997, 423.
11. H. G. Aurich, M. Boutahar, H. Köster, K.-D. Möbus and L. Ruiz, Chem. Ber., 1990, 123, 1999 See also S. Baskaran, H. G. Aurich, F. Biesemeier and K. Harms, J. Chem. Soc., Perkin Trans. 1, 1998, 3717; H. G. Aurich, M. Geiger, C. Gentes, K. Harms and H. Köster, Tetrahedron, 1998, 54, 3181.
12. For a preliminary communication see M. B. Gravestock, D. W. Knight, J. S. Lovell and S. R. Thornton, J. Chem. Soc., Perkin Trans. 1, 1994, 1661.
13. Cf. B. B. Snider and R. A. H. F. Hui, J. Org. Chem., 1985, 50, 5167.
14. J. Herscovici, M.-J. Egron and K. Antonakis, J. Chem. Soc., Perkin Trans. 1, 1982, 1967.
15. C. Huynh, F. Derguini-Boumechal and G. Linstrumelle, Tetrahedron Lett., 1979, 1503.
16. Cf. C. B. Rose and C. W. Smith, J. Chem. Soc., Chem. Commun., 1969, 248.
17. T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885 (Org. React., 1994, 46, 105).
18. M. Sodeoka, H. Yamada and M. Shibasaki, J. Am. Chem. Soc., 1990, 112, 4906; H. M. Hull and D. W. Knight, J. Chem. Soc., Perkin Trans. 1, 1997, 857.
19. W. C. Still, J. Am. Chem. Soc., 1978, 100, 1481; D. Seyferth and S. B. Andrews, J. Organomet. Chem., 1971, 30, 151.
20. D. Carpita and A. Rossi, Synthesis, 1982, 469.
21. T. Reichstein, A. Pedolin and A. Grussner, Helv. Chim. Acta, 1935, 18, 598.
22. J. Grundy, B. G. James and G. Pattenden, Tetrahedron Lett., 1972, 757.
23. D. L. J. Clive and C. G. Russell, J. Chem. Soc., Chem. Commun., 1981, 434.
24. D. Swern, A. J. Mancuso and S.-L. Huang, J. Org. Chem., 1978, 43, 2480.
25. W. P. Grith and S. V. Ley, Aldrichimica Acta, 1990, 23, 13; S. V. Ley, J. Norman, W. P. Griths and S. P. Marsden, Synthesis, 1994, 639.
26. W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Butterworth Heinemann, Oxford, 1996.
27. G. Hirth and R. Barner, Helv. Chim. Acta, 1982, 65, 1059; J. M. Klunder, S. Y. Ko and K. B. Sharpless, J. Org. Chem., 1986, 51, 3710.
28. Cf. B. H. Lipschutz, R. Moretti and R. Crow, Org. Synth., 1990, 69, 80.