Domino reaction: Pd(II)-catalyzed cyclization of unsaturated polyols and cross-coupling

Tetrahedron Asymmetry

Volumn 23, Issue 11-12, 2012, Pages 818-827

  Lásiková, Angelika ^a   Doháňošová, Jana ^a,b   Hlavínová, Lucia ^a   Toffano, Martial ^b   Vo Thanh, Giang ^b   Kožíšek, Jozef ^a   Gracza, Tibor ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BROMINE DERIVATIVE; HYDROXYL GROUP; PALLADIUM; POLYOL; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; DOMINO REACTION; HYDROXYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84864275360     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.05.020     Document Type: Article

References (74)

1. L.S. Hegedus Tetrahedron 40 1984 2415 2434
2. L.S. Hegedus Coord. Chem. Rev. 147 1996 443 545
3. A. Heumann, and M. Réglier Tetrahedron 52 1996 9289 9346
4. L.S. Hegedus Coord. Chem. Rev. 161 1997 129 255
5. L.S. Hegedus Coord. Chem. Rev 175 1998 159 270
6. J. Muzart Tetrahedron 61 2005 4179 4212
7. J. Muzart Tetrahedron 61 2005 5955 6008
8. J. Muzart Tetrahedron 61 2005 9423 9463
9. J. Muzart J. Mol. Catal. A: Chem. 319 2010 1 29
10. E.M. Beccalli, G. Broggini, A. Fasana, and M. Rigamonti J. Organomet. Chem. 696 2011 277 295
11. P. Kapitán, and T. Gracza Arkivoc viii 2008 8 17
12. P. Kapitán, and T. Gracza Tetrahedron: Asymmetry 19 2008 38 44
13. P. Szolcsányi, and T. Gracza Chem. Commun. 2005 3948 3950
14. M. Babjak, Ľ. Remeň, P. Szolcsányi, P. Zálupský, M. Miklóš, and T. Gracza J. Organomet. Chem. 691 2006 928 940
15. M. Palík, O. Karlubíková, A. Lásiková, J. Kožíšek, and T. Gracza Eur. J. Org. Chem. 2009 709 715
16. T. Gracza, and V. Jäger Synlett 1992 191 193
17. M.F. Semmelhack, and W.R. Epa Tetrahedron Lett. 34 1993 7205 7208
18. L.F. Tietze, K.M. Sommer, J. Zinngrebe, and F. Stecker Angew. Chem., Int. Ed. 44 2005 257 259
19. L.F. Tietze, F. Stecker, J. Zinngrebe, and K. Sommer Chem. Eur. J. 12 2006 8770 8776
20. L.F. Tietze, D.A. Spiegl, F. Stecker, J. Major, C. Raith, and C. Große Chem. Eur. J. 14 2008 8956 8963
21. For reviews see: J.P. Wolfe Eur. J. Org. Chem. 2007 571 582
22. J.P. Wolfe Synlett 2008 2913 2937
23. J.P. Wolfe, and M.A. Rossi J. Am. Chem. Soc. 126 2004 1620 1621
24. M.B. Hay, A.R. Hardin, and J.P. Wolfe J. Org. Chem. 70 2005 3099 3107
25. M.B. Hay, and J.P. Wolfe J. Am. Chem. Soc. 127 2005 16468 16476
26. M.B. Hay, and J.P. Wolfe Tetrahedron Lett. 47 2006 2793 2796
27. A.F. Ward, and J.P. Wolfe Org. Lett. 12 2010 1268 1271
28. J.E. Ney, and J.P. Wolfe Angew. Chem., Int. Ed. 43 2004 3605 3608
29. R. Lira, and J.P. Wolfe J. Am. Chem. Soc. 126 2004 13906 13907
30. M. Beaudoin Bertrand, and J.P. Wolfe Tetrahedron 61 2005 6447 6459
31. J.E. Ney, and J.P. Wolfe J. Am. Chem. Soc. 127 2005 8644 8651
32. Q. Yang, J.E. Ney, and J.P. Wolfe Org. Lett. 7 2005 2575 2578
33. J.E. Ney, M.B. Hay, Q. Yang, and J.P. Wolfe Adv. Synth. Catal. 347 2005 1614 1620
34. M. Beaudoin Bertrand, and J.P. Wolfe Org. Lett. 8 2006 2353 2356
35. M. Beaudoin Bertrand, M.L. Leathen, and J.P. Wolfe Org. Lett. 9 2007 457 460
36. M. Beaudoin Bertrand, J.D. Neukom, and J.P. Wolfe J. Org. Chem. 73 2008 8851 8860
37. J.D. Neukom, N.S. Perch, and J.P. Wolfe J. Am. Chem. Soc. 132 2010 6276 6277
38. B.R. Rosen, J.E. Ney, and J.P. Wolfe J. Org. Chem. 75 2010 2756 2759
39. D.N. Mai, and J.P. Wolfe J. Am. Chem. Soc. 132 2010 12157 12159
40. G.S. Lemen, and J.P. Wolfe Org. Lett. 12 2010 2322 2325
41. D.N. Mai, B.R. Rosen, and J.P. Wolfe Org. Lett. 13 2011 2932 2935
42. J.A. Fritz, J.S. Nakhla, and J.P. Wolfe Org. Lett. 8 2006 2531 2534
43. J.A. Fritz, and J.P. Wolfe Tetrahedron 64 2008 6838 6852
44. M.B. Hay, and J.P. Wolfe Angew. Chem., Int. Ed. 46 2007 6492 6494
45. G.S. Lemen, N.C. Giampietro, M.B. Hay, and J.P. Wolfe J. Org. Chem. 74 2009 2533 2540
46. A.F. Ward, and J.P. Wolfe Org. Lett. 13 2011 4728 4731
47. N.C. Giampietro, and J.P. Wolfe J. Am. Chem. Soc. 130 2008 12907 12911
48. J.S. Nakhla, and J.P. Wolfe Org. Lett. 9 2007 3279 3282
49. J.S. Nakhla, D.M. Schultz, and J.P. Wolfe Tetrahedron 65 2009 6549 6570
50. M.L. Leathen, B.R. Rosen, and J.P. Wolfe J. Org. Chem. 74 2009 5107 5110
51. J.D. Neukom, A.S. Aquino, and J.P. Wolfe Org. Lett. 13 2011 2196 2199
52. M.F. Semmelhack, C. Bodurow, and M. Baum Tetrahedron Lett. 25 1984 3171 3174
53. M.F. Semmelhack, C. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler, and M. Meier Pure Appl. Chem. 62 1990 2035 2040
54. T. Ling, Ch. Chowdhury, B.A. Kramer, and G.V. Binh J. Org. Chem. 66 2001 8843 8853
55. J. Song, and R.I. Hollingsworth Tetrahedron: Asymmetry 12 2001 387 391
56. A. Barco, N. Baricordi, S. Benetti, C. De Risi, G.P. Pollini, and V. Zanirato Tetrahedron 63 2007 4278 4283
57. V. Jäger, and B. Häfele Synthesis 1987 801 806
58. J. Robertson, W.P. Unsworth, and S.G. Lamont Tetrahedron 66 2010 2363 2372
59. J.K. Gallos, Ch.I. Stathakis, M.J. Salapassidou, C.E. Grammatoglou, and A.E. Koumbis Carbohydr. Res. 342 2007 744 748
60. A. Hall, K.P. Meldrum, P.R. Therond, and R.H. Wightman Synlett 1997 123 125
61. M. Yang, W. Ye, and S.W. Schneller J. Org. Chem. 69 2004 3993 3996
62. P. Va, and W.R. Roush Tetrahedron 63 2007 5768 5796
63. T. Gracza, T. Hasenöhrl, U. Stahl, and V. Jäger Synthesis 1991 1108 1118
64. M. Babjak, P. Zálupský, and T. Gracza Arkivoc v 2005 45 57
65. T. Gracza, and V. Jäger Synthesis 1994 1359 1368
66. D.J. Dixon, S.V. Ley, T. Gracza, and P. Szolcsányi J. Chem. Soc., Perkin Trans. 1 8 1999 839 841
67. M. Babjak, P. Kapitán, and T. Gracza Tetrahedron Lett. 43 2002 6983 6985
68. M. Babjak, P. Kapitán, and T. Gracza Tetrahedron 61 2005 2471 2479
69. L. Bellovičová, J. Kožíšek, J. Doháňošová, A. Lásiková, and T. Gracza Acta Crystallogr., Sect. E 66 9 2010 O2381 U930
70. CCDC-88254 (for cis-15) and CCDC-882585 [for compound 21b] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
71. G. Cardillo, and M. Orena Tetrahedron 46 1990 3321 3408
72. M. Orena 4th ed. G. Helmchen, R. Hoffmann, J. Mulzer, Houben-Weyl Vol. 2 1995 Thieme Stuttgart 4698 4817
73. A.R. Chamberlin, R.L. Mulholland Jr., S.D. Kahn, and W.J. Hehre J. Am. Chem. Soc. 109 1987 672 677
74. S.D. Kahn, and W.J. Hehre J. Am. Chem. Soc. 109 1987 666 671