Intermolecular nitroso Diels-Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium

Organic and Biomolecular Chemistry

Volumn 3, Issue 24, 2005, Pages 4395-4401

  Calvet, Géraldine ^a   Guillot, Régis ^a   Blanchard, Nicolas ^a   Kouklovsky, Cyrille ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; MOLECULAR DYNAMICS; NITROGEN COMPOUNDS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

AMINOALCOHOLS; DIELS-ALDER CYCLOADDITION; PRODUCT DISTRIBUTION;

DERIVATIVES;

BETULACEAE;

EID: 29844440317     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b513397a     Document Type: Article

References (63)

1. O. Wichterle, Collect. Czech. Chem. Commun., 1947, 12, 292.
2. (a) P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317;
3. (b) L. F. Tietze and G. Kettschau, Top. Curr. Chem., 1997,189, 1;
4. (c) J. Streith and A. Defoin, Synlett, 1996, 189;
5. (d) C. Kibayashi and S. Aoyagi, Synlett, 1995, 873;
6. (e) P. Zuman and B Shah, Chem. Rev., 1994, 94, 1621;
7. (f) J. Streith and A. Defoin, Synthesis, 1994, 1107;
8. (g) H. Waldmann, Synthesis, 1994, 535;
9. (h) S. M. Weinreb and R. R. Staib, Tetrahedron, 1982, 38, 3087;
10. (i) S. M. Weinreb, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon Press, New York, 1991, p. 401;
11. (j) G. W. Kirby, Chem. Soc. Rev., 1977, 6, 1.
12. H. Yamamoto and N. Momiyama, Chem. Commun., 2005, 3514.
13. S. Kumarn, D. M. Shaw, D. A. Longbottom and S. V. Ley, Org. Lett., 2005, 7, 4189.
14. (a) C. P. Chow and K. J. Shea, J. Am. Chem. Soc., 2005, 127, 3678;
15. (b) Y. Yamamoto and H. Yamamoto, J. Am. Chem. Soc., 2004, 126, 4128.
16. G. Calvet, M. Dussaussois, N. Blanchard and C. Kouklovsky, Org. Lett., 2004, 6, 2449.
17. (a) C.-J. Li, Chem. Rev., 2005, 105, 3095;
18. (b) D. Sinou, Adv. Synth. Catal., 2002, 344, 221;
19. (c) U. M. Lindström, Chem. Rev., 2002, 102, 2751;
20. (d) T. Laziridis, Acc. Chem. Res., 2001, 34, 931;
21. (e) F. Fringuelli, O. Piermatti, F. Pizzo and L. Vaccaro, Eur. J. Org. Chem., 2001, 439;
22. (f) J. B. F. N. Engberts and M. J. Blandamer, Chem. Commun., 2001, 1701;
23. (g) S. Otto and J. B. F. N. Engberts, Pure Appl. Chem., 2000, 72, 1365;
24. (h) S. Kong and J. D. Evanseck, J. Am. Chem. Soc., 2000, 122, 10418;
25. (i) C. Cativiela, J. I. Garcia, J. Gil, R. M. Martinez, J. A. Mayoral, L. Salvatella, J. S. Urieta, A. M. Mainar and M. H. Abraham, J. Chem. Soc., Perkin Trans. 2, 1997, 653;
26. (j) C. Cativiela, J. I. Garcia, J. A. Mayoral and L. Salvatella, Chem. Soc. Rev., 1996, 209;
27. (k) A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741;
28. (l) J. F. Blake, D. Lim and W. L. Jorgensen, J. Org. Chem., 1994, 59, 803;
29. (m) S. Arseniyadis, R. Rodriguez, D. V. Yashunsky, J. Camara and G. Ourisson, Tetrahedron Lett., 1994, 35, 4843;
30. (n) R. Breslow, Acc. Chem. Res., 1991, 24, 159.
31. F. Fringuelli, O. Piermatti, F. Pizzo, Targets in Heterocyclic Systems -Chemistry and Properties, ed. O. A. Attanasi and D. Spinelli, Italian Society of Chemistry, Rome, Italy, 1997, vol. 1, ch. 5, p. 57.
32. (a) T. Ozawa, S. Aoyagi and C. Kibayashi, J. Org. Chem., 2001, 66, 3338;
33. (b) C. Kibayashi and S. Aoyagi, Synlett, 1995, 873.
34. A. D. Cohen, B.-B. Zeng, S. B. King and J. P Toscano, J. Am. Chem. Soc., 2003, 125, 1444.
35. A. Hall, P. D. Bailey, D. C. Rees, G. M. Rosair and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 2000, 329.
36. J. W. Wijnen and J. B. F. N. Engberts, Liebigs Ann./Recl., 1997, 1085.
37. M. Majewski, D. M. Gleave and P. Nowak, Can. J. Chem., 1995, 73, 1616.
38. (a) C. Czekelius and E. M. Carreira, Angew. Chem., Int. Ed., 2005, 44, 612;
39. (b) I. P. Beletskaya, A. L. Kurts and O. A. Reutov, Ambident Anions, Plenum Publishing Corporation, New York, 1983, ch. 4, p. 176.
40. Azoxy derivatives are known to be formed from nitroso species or from the corresponding azodioxy species. For an example under oxidative conditions, see: A. G. Hortmann and R. E. Youngstrom, J. Am. Chem. Soc., 1969, 34, 3392.
41. (a) S. Kobayashi and K. Manabe, Acc. Chem. Res., 2002, 35, 209;
42. (b) K. Mikami, M. Terada and H. Matsuzawa, Angew. Chem., Int. Ed., 2002, 41, 3554;
43. (c) S. Kobayashi, Eur. J. Org. Chem., 1999, 15.
44. Experimental data (not shown) for the cycloaddition of 1 in anhydrous media tend to indicate that Lewis acids accelerate the N-O bond cleavage reaction of dihydrooxazines (cf. Scheme 3). Analogous behaviour may be operative for the cycloaddition reaction of 1 in aqueous media, thereby leading to lower product selectivity.
45. A. G. Leach and K. N. Houk, J. Org. Chem., 2001, 66, 5192.
46. Stereochemistry determined by extensive multinuclear 2D NMR.
47. J. B. F. N. Engberts, T. A. J. W. Wajer, C. Kruk and T. J. De Boer, Recl. Trav. Chim. Pays-Bas, 1969, 88, 795.
48. G. W. Kirby and M. Nazeer, J. Chem. Soc., Perkin Trans. 1, 1993, 1397;
49. G. W. Kirby and M. Nazeer, Tetrahedron Lett., 1988, 29, 6173;
50. C. C. Christie, G. W. Kirby, H. McGuigan and J. W. M. Mackinnon, J. Chem. Soc., Perkin Trans. 1, 1985, 2469.
51. J. P. Muxworthy, J. A. Wilkinson and G. Procter, Tetrahedron Lett., 1995, 36, 7535;
52. A. Miller and G. Procter, Tetrahedron Lett., 1990, 31, 1041.
53. 2-Aryl-1,3-cyclohexadiene derivatives are known to decompose rapidly in the presence of oxygen: P. J. Grisdale, T. H. Regan, J. C. Doty, J. Figueras and J. L. R. Williams. J. Org. Chem., 1968, 33, 1116.
54. The mechanism accounting for the N-O bond cleavage reaction (see ref. 6) has been revised to account for recent experimental observations. Further studies along these lines are in progress and will be reported in due course.
55. E. M. Gonzalez-Garcia, J. Grognux, D. Wahler and J.-L. Reymond, Helv. Chim. Acta, 2003, 86, 2458.
56. (a) G. Calvet, N. Blanchard and C. Kouklovsky, Synthesis, 2005, DOI: 10.155/s-2005-918457;
57. (b) D. Zhang, C. Süling and M. J. Miller, J. Org. Chem., 1998, 63, 885.
58. A. Amrollah-Madjdabadi, R. Beugelmans and A. Lechevallier, Synthesis, 1986, 826.
59. Z. Eckstein, Chem. Abstr., 1957, 8754.
60. G. A. Smirnov, A. M. Vasil'ev and O. A. Luk'yanov, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl), 1991, 40, 2523.
61. G. B. Linden and M. H. Gold, J. Org. Chem., 1956, 21, 1175.
62. A. Sofia, E. Karlström, M. Rönn, A. Thorarensen and J.-E. Bäckvall, J. Org. Chem., 1998, 63, 2517.
63. S. W. Baldwin and J. S. Debenham, Org. Lett., 2000, 2, 99.