Application of pyranoside phosphite-pyridine ligands to enantioselective metal-catalyzed allylic substitutions and conjugate 1,4-additions

Tetrahedron Asymmetry

Volumn 24, Issue 17, 2013, Pages 995-1000

  Lega, Matteo ^a,b   Margalef, Jessica ^c   Ruffo, Francesco ^a,b   Pàmies, Oscar ^c   Diéguez, Montserrat ^c  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b Consorzio Interuniversitario di Reattività Chimica e Catalisi ^*  (Italy)

^c UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; COPPER; PALLADIUM; PHOSPHITE; PYRANOSIDE; PYRIDINE DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; ENANTIOSELECTIVITY; HYDROLYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84883356166     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.06.011     Document Type: Article

References (81)

1. For reviews, see: J. Tsuji Palladium Reagents and Catalysis Innovations in Organic Synthesis 1995 Wiley New York
2. B.M. Trost, and D.L. van Vranken Chem. Rev. 96 1996 395
3. M. Johannsen, and K.A. Jorgensen Chem. Rev. 98 1998 1689
4. A. Pfaltz, and M. Lautens E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis Vol. 2 1999 Springer Berlin Chapter 24
5. G. Helmchen, and A. Pfaltz Acc. Chem. Res. 33 2000 336
6. A.M. Masdeu-Bultó, M. Diéguez, E. Martín, and M. Gómez Coord. Chem. Rev. 242 2003 159
7. B.M. Trost, and M.L. Crawley Chem. Rev. 103 2003 2921
8. E. Martín, and M.C.R. Diéguez Chemie 10 2007 188
9. Z. Lu, and S. Ma Angew. Chem., Int. Ed. 47 2008 258
10. M. Diéguez, and O. Pàmies Acc. Chem. Res. 43 2010 312
11. For reviews, see: A. Alexakis, and C. Benhaim Eur. J. Org. Chem. 2002 3221
12. A. Alexakis Methodologies in Asymmetric Catalysis 2004 American Chemical Society Washington DC Chapter 4
13. J. Christoffers, G. Koripelly, A. Rosiak, and M. Rössle Synthesis 2007 1279
14. O.M. Berner, L. Tedeschi, and D. Enders Eur. J. Org. Chem. 2002 1877
15. B.L. Feringa, R. Naasz, R. Imbos, and L.A. Arnold N. Krause, Modern Organocopper Chemistry 2002 Wiley-VCH Weinheim Germany 224 258
16. N. Krause, and A. Hoffmann-Röder Synthesis 2001 171
17. A.H. Hoveyda, A.W. Hird, and M.A. Kacprzynski Chem. Commun. 2004 1779
18. M.P. Sibi, and S. Manyem Tetrahedron 56 2000 8033
19. F. López, A.J. Minnarrd, and B.L. Feringa Acc. Chem. Res. 40 2007 179
20. T.T.L. Au-Yeung, S.S. Chan, and A.S.C. Chan Adv. Synth. Catal. 345 2003 537
21. S. Woodward Chem. Soc. Rev. 29 2000 393
22. A. Alexakis, J.E. Bäckvall, N. Krause, O. Pàmies, and M. Diéguez Chem. Rev. 108 2008 2796
23. C. Hawner, and A. Alexakis Chem. Commun. 46 2010 7295
24. For reviews within this field of research, see D. Steinborn, and H. Junicke Chem. Rev. 100 2000 4283
25. M. Diéguez, O. Pàmies, A. Ruiz, Y. Díaz, S. Castillón, and C. Claver Coord. Chem. Rev. 248 2004 2165
26. M. Diéguez, O. Pàmies, and C. Claver Chem. Rev. 104 2004 3189
27. Y. Díaz, S. Castillón, and C. Claver Chem. Soc. Rev. 34 2005 702
28. M. Diéguez, C. Claver, and O. Pàmies Eur. J. Org. Chem. 2007 4621
29. M. Diéguez, and O. Pàmies Chem. Eur. J. 2008 944
30. M.M.K. Boysen Chem. Eur. J. 13 2007 8648
31. V. Benessere, A. De Roma, R. Del Litto, and F. Ruffo Coord. Chem. Rev. 254 2010 390
32. S. Woodward, M. Diéguez, and O. Pàmies Coord. Chem. Rev. 2010 2007 254
33. For representative examples, see: B. Gläser, and H. Kunz Synlett 1998 53
34. K. Yonehara, T. Hashizume, K. Mori, K. Ohe, and S. Uemura Chem. Commun. 1999 415
35. K. Yonehara, T. Jashizume, K. Mori, K. Ohe, and S. Uemura J. Org. Chem. 64 1999 9374
36. K. Yonehara, K. Mori, T. Hashizume, K.G. Chung, K. Ohe, and S. Uemura J. Organomet. Chem. 603 2000 40
37. C. Borriello, M.E. Cucciolito, A. Panunzi, and F. Ruffo Inorg. Chim. Acta 353C 2003 238
38. J. Mazuela, P.-O. Norrby, P.G. Andersson, O. Pàmies, and M. Diéguez J. Am. Chem. Soc. 133 2011 13634
39. Y. Mata, Y. Pàmies, and M. Diéguez Chem. Eur. J. 13 2007 3296
40. Y. Mata, O. Pàmies, M. Diéguez, and C. Claver Adv. Synth. Catal. 2005 1943 347
41. Y. Mata, O. Pàmies, and M. Diéguez Adv. Synth. Catal. 351 2009 3217
42. Y. Mata, M. Diéguez, O. Pàmies, and C. Claver Org. Lett. 7 2005 5597
43. M. Diéguez, J. Mazuela, O. Pàmies, J.J. Verendel, and P.G. Andersson J. Am. Chem. Soc. 130 2008 7208
44. A. Börner Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications Vol. 2 2008 Wiley-VCH and references therein
45. P. Espinet, and K. Soulantica Coord. Chem. Rev. 193 1999 499
46. P. Molina, A. Arques, A. García, and M.C. Ramríez de Arellano Eur. J. Inorg. Chem. 1988 1359 and references therein
47. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1988 9722
48. A. Aranyos, D.W. Old, A. Kiyomori, J.P. Wolfe, J.P. Sadighi, and S.L. Buchwald J. Am. Chem. Soc. 121 1989 4369
49. C. Amatore, A. Fuxa, and A. Jutand Chem. Eur. J. 6 2000 1474
50. For some exemple, see: G. Chelucci, G. Orrù, and G.A. Pinna Tetrahedron 59 2003 9471
51. P.W.N.M. van Leeuwen, P.C.J. Kamer, C. Claver, O. Pàmies, and M. Diéguez Chem. Rev. 111 2011 2077
52. For successful examples, see for instance: H. Wan, Y. Hu, Y. Liang, S. Gao, J. Wang, Z. Zheng, and X. Hu J. Org. Chem 68 2003 8277 (Cu-conjugate addition)
53. X. Luo, Y. Hu, and X. Hu Tetrahedron: Asymmetry 16 2005 1227 (Cu-conjugate addition)
54. J. Mazuela, O. Pàmies, and M. Diéguez Chem. Eur. J. 19 2013 2416 (Pd-allylic substituion)
55. Mazuela, J.; Pàmies, O.; Diéguez, M. Adv. Synth. Catal. doi: http://dx.doi.org/10.1002/adsc.201201017 (Ir-hydrogenation).
56. J. Margalef, M. Lega, F. Ruffo, O. Pàmies, and M. Diéguez Tetrahedron: Asymmetry 23 2012 945
57. A recent report described the synthesis of closely related ligands, see: H. Xia, H. Yan, C. Shen, and P. Zhang Catal. Commun. 16 2011 155
58. O. Pàmies, M. Diéguez, G. Net, A. Ruiz, and C. Claver Organometallics 19 2000 1488
59. J.Y. Baek, Y. Shin, H.B. Jeon, and K.S. Kim Tetrahedron Lett. 46 2005 5143
60. V. Benessere, A. De Roma, and F. Ruffo ChemSusChem 1 2008 425
61. A.M. Porte, J. Reinbenspies, and K. Burgess J. Am. Chem. Soc. 120 1998 9180
62. B.M. Trost, and D.L. Van Vranken Angew. Chem., Int. Ed. 31 1992 228
63. B.M. Trost, and D.L. Van Vranken J. Am. Chem. Soc. 115 1993 444
64. B.M. Trost, and B. Breit Tetrahedron Lett. 35 1994 5817
65. B.M. Trost, B. Breit, S. Peukert, J. Zambrano, and J.W. Ziller Angew. Chem., Int. Ed. Engl. 34 1995 2386
66. B.M. Trost, and D.E. Patterson J. Org. Chem. 63 1998 1339
67. S. Lee, C.W. Lim, C.E. Song, K.M. Kim, and C.H. Jun J. Org. Chem. 64 1999 4445
68. C.W. Lim, and S. Lee Tetrahedron 56 2000 5135
69. B.M. Trost, J. Zambrano, and W. Ritcher Synlett 2001 907
70. N. Buschmann, A. Rueckert, and S. Blechert J. Org. Chem. 67 2002 4325
71. C.E. Song, J.W. Yang, E.J. Roh, S.G. Lee, J.H. Ahn, and H. Han Angew. Chem., Int. Ed. 41 2002 3852
72. B.M. Trost, Z. Pan, J. Zambrano, and G. Kujat Angew. Chem., Int. Ed. 41 2002 4691
73. A. Agarkov, E.W. Uffman, and S.R. Gibeltson Org. Lett. 5 2003 2091
74. D. Zhao, Z. Wang, and K. Ding Synlett 2005 2067
75. O. Pàmies, M. Diéguez, G. Net, A. Ruiz, and C. Claver Tetrahedron: Asymmetry 11 2000 4377
76. A. Alexakis, C. Benhaim, S. Rosset, and M. Humam J. Am. Chem. Soc. 124 2002 5262
77. T. Jongsma, D. Fossen, G. Challa, and P.W.N.M. van Leeuwen J. Mol. Catal. 83 1993 17
78. O. Pàmies, G.P.F. van Strijdonck, M. Diéguez, S. Deerenberg, G. Net, A. Ruiz, C. Claver, P.C.J. Kamer, and P.W.N.M. van Leeuwen J. Org. Chem. 66 2001 8867
79. M.A. Pericàs, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gómez, F. Jiménez, G. Muller, and M. Rocamora Chem. Eur. J. 8 2002 4164
80. D.A. Evans, K.R. Campos, J.S. Tedrow, F.E. Michael, and M.R. Gagné J. Am. Chem. Soc. 122 2000 7905
81. A. Alexakis, V. Albrow, K. Biswas, M. d'Augustin, O. Prieto, and S. Woodward Chem. Commun. 2005 2843