Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems

Tetrahedron

Volumn 62, Issue 8, 2006, Pages 1717-1725

  Sarabèr, Florence C E ^a   Dratch, Svetlana ^b   Bosselaar, Geke ^a   Jansen, Ben J M ^a   De Groot, Aede ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

Carvone; Domino reactions; Mukaiyama Michael addition; Tricyclic systems

Indexed keywords

CARVONE; CYCLOHEXANONE; CYCLOPENTANONE DERIVATIVE; ETHER DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; MUKAIYAMA MICHAEL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 31544483650     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.059     Document Type: Article

References (45)

1. H. Paulsen, S. Antons, A. Brandes, M. Lögers, S.N. Müller, P. Naab, C. Schmeck, S. Schneider, and J. Stoltefuss Angew. Chem., Int. Ed. 38 1999 3373
2. H. Hagiwara, Y. Yamada, H. Sakai, T. Suzuki, and M. Ando Tetrahedron 54 1998 10999
3. I. Prowotorow, W. Stepanenko, and J. Wicha Eur. J. Org. Chem. 2002 2727
4. E. Gorobets, Z. Urbanczyk-Lipkowska, V. Stepanenko, and J. Wicha Tetrahedron Lett. 42 2001 1135
5. E. Gorobets, M.S. Miftakhov, and F.A. Valeev Russ. Chem. Rev. 69 2000 1001
6. W. Stepanenko, and J. Wicha Tetrahedron Lett. 39 1998 885
7. S. Marczak, K. Michalak, Z. Urbanczyk-Lipkowska, and J. Wicha J. Org. Chem. 63 1998 2218
8. S. Marczak, and J. Wicha Tetrahedron Lett. 34 1993 6627
9. P. Grzywacz, S. Marczak, and J. Wicha J. Org. Chem. 62 1997 5293
10. S. Kobayashi, and T. Mukaiyama Chem. Lett. 1986 221
11. H. Hagiwara, A. Okano, and H. Uda J. Chem. Soc., Chem. Commun. 1985 1047
12. G.H. Posner Chem. Rev. 86 1986 831
13. G.H. Posner, and E. Asirvatham Tetrahedron Lett. 27 1986 663
14. G.H. Posner, S.B. Lu, and E. Asirvatham Tetrahedron Lett. 27 1986 659
15. G.H. Posner, S.B. Lu, E. Asirvatham, E.F. Silversmith, and E.M. Shulman J. Am. Chem. Soc. 108 1986 511
16. C. Wakselman, and M. Mondon Tetrahedron Lett. 14 1973 4285
17. T. Mukaiyama, K. Banno, and K. Narasaka J. Am. Chem. Soc. 96 1974 7503
18. K. Narasaka, K. Soai, Y. Aikawa, and T. Mukaiyama Bull. Chem. Soc. Jpn. 49 1976 779
19. S. Kobayashi, M. Murakami, and T. Mukaiyama Chem. Lett. 1985 953
20. S. Kobayashi Eur. J. Org. Chem. 1999 15
21. J. Cossy, F. Lutz, V. Alauze, and C. Meyer Synlett 2002 45
22. J. Chen, and J. Otera Tetrahedron 53 1997 14275
23. T. Sato, Y. Wakahara, J. Otera, and H. Nozaki Tetrahedron 47 1991 9773
24. A. Bernardi, G. Colombo, and C. Scolastico Tetrahedron Lett. 37 1996 8921
25. P.A. Grieco, R.J. Cooke, K.J. Henry, and J.M. VanderRoest Tetrahedron Lett. 32 1991 4665
26. T. Harada, H. Iwai, H. Takatsuki, and K. Fujita Org. Lett. 3 2001 2101
27. P. Van de Weghe, and J. Collin Tetrahedron Lett. 34 1993 3881
28. H. Kooijman, F.C.E. Saraber, A. de Groot, and A.L. Spek Acta Crystallogr., Sect. E 61 2005 3921 for compound 10a. Spek, A. L.; Menzer, S.; Meulemans, T.; de Groot, A. CCDC 227434 for compound 13b and CCDC227438 for compound 13a
29. C.H. Heathcock, M.H. Norman, and D.E. Ühling J. Am. Chem. Soc. 107 1985 2797
30. C.H. Heathcock, and D.E. Ühling J. Org. Chem. 51 1986 279
31. This one-pot procedure is termed a domino reaction although not all reagents are present in the reaction mixture from the start. On the other hand, the reaction conditions remain the same during the whole reaction time and for this reason, we estimate this term appropriate for the situation.
32. G. Quinkert, M.d. Grosso, A. Bucher, J.W. Bats, and G. Dürner Tetrahedron Lett. 32 1991 3357
33. G.H. Posner, J.P. Mallamo, and A.Y. Black Tetrahedron 37 1981 3921
34. I.N. Nazarov, I.V. Torgov, and G.P. Verkholetova Dokl. Akad. Nauk SSSR 112 1957 1067
35. K. Mikami, K. Takahashi, and T. Nakai J. Am. Chem. Soc. 112 1990 4035
36. M.E. Jung, and K.M. Halweg Tetrahedron Lett. 25 1984 2121
37. V. Gauthier, B. Cazes, and J. Goré Tetrahedron Lett. 32 1991 915
38. J. Das, R. Kubela, G.A. MacAlpine, Z. Stojanac, and Z. Valenta Can. J. Chem. 57 1979 3308
39. S. Dratch, T. Charnikhova, F.C.E. Sarabèr, B.J.M. Jansen, and A. de Groot Tetrahedron 59 2003 4287
40. P.A. Grieco, S.A. May, and M.D. Kaufman Tetrahedron Lett. 39 1998 7047
41. J. Hydrio, P. van de Weghe, and J. Collin Synthesis 1997 68
42. I. Kopka, and M.W. Rathke J. Org. Chem. 46 1981 3771
43. O.A. Kruglaya, L.I. Belousova, D.V. Gendin, I.D. Kalikhman, and N.S. Vyazankin J. Organomet. Chem. 201 1980 69
44. S.P. Hong, H.A. Lindsay, T. Yaramasu, X. Zhang, and M.C. McIntosh J. Org. Chem. 67 2002 2042
45. P. Cazeau, F. Duboudin, F. Moulines, O. Babot, and J. Dunogues Tetrahedron 43 1987 2075