Asymmetric Induction in the Cycloaddition of a Masked p-Benzoquinone to Cyclic Nitrones

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7781-7787

  De March, Pedro ^a   Escoda, Maria ^a   Figueredo, Marta ^a   Font, Josep ^a   Alvarez Larena, Angel ^a   Piniella, Juan F ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000677202     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971035t     Document Type: Article

References (53)

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15. Reviews in the cycloaddition chemistry of nitrones: (a) Tufariello, J. J. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley and Sons: New York, 1984; Vol. 2, Chapter 9. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH Verlagsgesellschaft: Weinheim, 1988. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L. Gazz. Chim. Ital. 1989, 119, 253.
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26. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
27. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
28. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
29. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
30. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
31. Target molecules prepared from quinone monoketals include neolignans: (a) Büchi, G.; Mak, C. P. J. Am. Chem. Soc. 1977, 99, 8073. (b) Büchi, G.; Chu, P. S. J. Org. Chem. 1978, 43, 3717; pentaprismanes: (c) Dauben, W. G.; Cunningham, Jr., A. F. J. Org. Chem. 1983, 48, 2842; anthracyclinones: (d) Chenard, B. L.; Dolson, M. G.; Sercel, A. D.; Swenton, J. S. J. Org. Chem. 1984, 49, 318. (e) Russell, R. A.; Gee, P. S.; Irvine, R. W.; Warrener, R. N. Aust. J. Chem. 1984, 37, 1709; aranorosin: (f) McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
32. de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1995, 60, 3895.
33. For a recent review on asymmetric cycloaddition reactions of nitrones to olefins see: Frederickson, M. Tetrahedron 1997, 53, 403.
34. Murahashi, S.-I.; Shiota, T. Tetrahedron Lett. 1987, 28, 2383.
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36. (b) Sabel, W. Chem. Ind. (London) 1966, 1261.
37. (a) Busqué, F.; Cid, P.; de March, P.; Figueredo, M.; Font, J. Heterocycles 1995, 40, 387.
38. (b) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097.
39. (c) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031.
40. Ketal 1a is commercially available. (a) Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891. (b) Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Synth. Commun. 1994, 24, 2989 and references therein.
41. Ketal 1a is commercially available. (a) Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891. (b) Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Synth. Commun. 1994, 24, 2989 and references therein.
42. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden; Springer Verlag: Berlin, 1976.
43. (a) Heller, J. E.; Dreiding, A. S.; O'Connor, B. R.; Simmons, H. E.; Buchanan, G. L.; Raphael, R. A.; Taylor, R. Helv. Chim. Acta 1973, 56, 272.
44. (b) Capparelli, M. P.; Swenton, J. S. J. Org. Chem. 1987, 52, 5360.
45. 8 at δ 6.60 and only compatible with the regiochemistry depicted in A. Chemical equation presented
46. The spectroscopic data do not allow us, however, to exclude the other possible regiochemistry (B), and although the regioisomer 6b would be the one expected on the basis of the FMO theory and of most precedents, the isolation of the 1:1 cycloadduct A in the same reaction makes the structure assigned to 6b only tentative. Chemical equation presented
47. Pirrung, M. C.; Nunn, D. S. Tetrahedron Lett. 1992, 33, 6591.
48. de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Medrano, J. An. Quim. Int. Ed. 1997, 93, 81.
49. In related compounds we have observed that N-benzylation yields cis-fused isoxazolidinium salts, independent of the preferred invertomer of the starting azabicyclic system. Sometimes this fact can help to elucidate the stereochemistry of these compounds. Although the benzylation of 11b gave as expected a unique cis-fused salt, its spectroscopic data were not enough to unequivocally assign its stereochemistry.
50. The authors have deposited atomic coordinates for lib with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
51. 5,6 measured for 10b are 9.5 and 6.6 Hz, in better agreement with a preference for the conformer C', in which only the cis-alkoxy group is axial, therefore making its face more sterically demanding. Chemical equation presented
52. 28 which will be published in due course. Accordingly, the absolute configuration of (+)-11b is (3S,4aS,10aR,10bR) and that of (-)-7, (4aS,10aR,10bR).
53. Gebauer, O.; Brückner, R. Liebigs Ann. 1996, 1559.