Highly selective asymmetric Rh-catalyzed hydroformylation of heterocyclic olefins

Journal of the American Chemical Society

Volumn 134, Issue 15, 2012, Pages 6607-6616

  Chikkali, Samir H ^a,b   Bellini, Rosalba ^a   De Bruin, Bas ^a   Van Der Vlugt, Jarl Ivar ^a   Reek, Joost N H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DUTCH POLYMER INSTITUTE DPI   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC HYDROFORMYLATION; CATALYST RESTING STATE; CATALYST SYSTEM; DIHYDROFURANS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; MILD REACTION CONDITIONS; REGIOISOMERS; SYN-GAS;

CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; HYDROFORMYLATION; HYDROXYLATION; OLEFINS; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS; REGIOSELECTIVITY; RHODIUM; SYNTHESIS GAS;

LIGANDS;

ALDEHYDE DERIVATIVE; ALKENE; PHOSPHINE DERIVATIVE; PYRROLINE DERIVATIVE; XANTHENE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HYDROFORMYLATION; HYPERBARISM; INFRARED SPECTROSCOPY; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84859977090     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210117z     Document Type: Article

References (108)

1. Nozaki, K. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Heidelberg, Germany, 1999; pp 381-416.
2. Claver, C.; Dieguez, M.; Pamies, O.; Castillon, S. Top. Organomet. Chem. 2006, 18, 35-64
3. van Leeuwen, P. W. N. M. Homogeneous Catalysis, Understanding the Art; Kluwer: Dordrecht, The Netherlands, 2004, pp 125-174.
4. Clarke, M. L. Curr. Org. Chem. 2005, 9, 701-718
5. Breit, B. Sci. Synth. 2007, 227-318
6. van Leeuwen, P. W. N. M.; Claver, C. Rhodium Catalyzed Hydroformylation; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2000.
7. Breeden, S.; Cole-Hamilton, D. J.; Foster, D. F.; Schwarz, G. J.; Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106-4108
8. Nettekoven, U.; Kamer, P. C. J.; Widhalm, M.; van Leeuwen, P. W. N. M. Organometallics 2000, 19, 4596-4607
9. Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259-268
10. van der Vlugt, J. I.; Bonet, J. M.; Mills, A. M.; Spek, A. L.; Vogt, D. Tetrahedron Lett. 2003, 44, 4389-4392
11. van der Vlugt, J. I.; Grutters, M. M. P.; Mills, A. M.; Kooijman, H.; Spek, A. L.; Vogt, D. Eur. J. Inorg. Chem. 2003, 4361-4369
12. Barbaro, P.; Bianchini, C.; Giambastiani, G.; Parisel, S. L. Coord. Chem. Rev. 2004, 248, 2131-2150
13. Clarkson, G. J.; Ansell, J. R.; Cole-Hamilton, D. J.; Pogorzelec, P. J.; Whittell, J.; Wills, M. Tetrahedron: Asymmetry 2004, 15, 1787-1792
14. Breit, B.; Breuninger, D. J. Am. Chem. Soc. 2004, 126, 10244-10245
15. Zijp, E. J.; van der Vlugt, J. I.; Tooke, D. M.; Spek, A. L.; Vogt, D. Dalton Trans. 2005, 512-517
16. Dahlenburg, L. Coord. Chem. Rev. 2005, 249, 2962-2992
17. Han, D.; Li, X.; Zhang, H.; Liu, Z.; Hu, G; Li, C. J. Mol. Catal. A: Chem. 2008, 283, 15-22
18. For a recent review on pharmaceutical building blocks via asymmetric hydroformylation, see: Chaudhari, R. V. Curr. Opin. Drug Discovery Dev. 2008, 11, 820-828 and references therein
19. van der Vlugt, J. I.; Sablong, R.; Mills, A. M.; Kooijman, H.; Spek, A. L.; Meetsma, A.; Vogt, D. Dalton Trans. 2003, 4690-4699
20. van der Vlugt, J. I.; Paulusse, J. M. J.; Zijp, E. J.; Tijmensen, J. A.; Mills, A. M.; Spek, A. L.; Claver, C.; Vogt, D. Eur. J. Inorg. Chem. 2004, 4193-4201
21. Kostas, I. D.; Vallianatou, K. A.; Holz, J.; Börner, A. Appl. Organomet. Chem. 2005, 19, 1090-1095
22. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Claver, C.; Pàmies, O.; Diéguez, M. Chem. Rev. 2011, 111, 2077-2118
23. Mikhel, I. S.; Dubrovina, N. V.; Shuklov, I. A.; Baumann, W.; Selent, D.; Jiao, H.; Christiansen, A.; Franke, R.; Börner, A. J. Organomet. Chem. 2011, 696, 3050-3057
24. Zou, Y.; Yan, Y.; Zhang, X. Tetrahedron Lett. 2007, 48, 4781-4784
25. Baber, R. A.; Haddow, M. F.; Middleton, A. J.; Orpen, A. G.; Pringle, P. G.; Haynes, A.; Williams, G. J.; Papp, R. Organometallics 2007, 26, 713-725
26. Ionescu, G.; van der Vlugt, J. I.; Abbenhuis, H. C. L.; Vogt, D. Tetrahedron: Asymmetry 2005, 16, 3970-3975
27. Dieguez, M.; Pamies, O.; Claver, C. Tetrahedron: Asymmetry 2004, 15, 2113-2122
28. van der Vlugt, J. I.; Ackerstaff, J.; Dijkstra, T. W.; Mills, A. M.; Kooijman, H.; Spek, A. L.; Meetsma, A.; Abbenhuis, H. C. L.; Vogt, D. Adv. Synth. Catal. 2004, 346, 399-412
29. Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A.; Petersen, J. L.; Abboud, K. A. J. Org. Chem. 2004, 69, 4031-4040
30. van der Vlugt, J. I.; Grutters, M. M. P.; Ackerstaff, J.; Hanssen, R. W. J. M.; Abbenhuis, H. C. L.; Vogt, D. Tetrahedron Lett. 2003, 44, 8301-8305
31. Slagt, V. F.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Angew. Chem., Int. Ed. 2003, 42, 5619-5623
32. Dieleman, C.; Kamer, P. C. J.; Reek, J. N. H.; van Leeuwen, P. W. N. M. Helv. Chim. Acta 2001, 84, 3269-3280
33. van Rooy, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Veldman, N.; Spek, A. L. Organometallics 1996, 15, 835-847
34. Buisman, G. J. H.; Vos, E.; Kamer, P. C.J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409-417
35. Pruett, R. L.; Smith, J. A. J. Org. Chem. 1969, 34, 327-330
36. Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423
37. Deerenberg, S.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 2000, 19, 2065-2072
38. Beghetto, V.; Scrivanti, A.; Matteoli, U. Catal. Commun. 2001, 2, 139-143
39. Arena, C. G.; Faraone, F.; Graiff, C.; Tiripicchio, A. Eur. J. Inorg. Chem. 2002, 711-716
40. Slagt, V. F.; Röder, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. J. Am. Chem. Soc. 2004, 126, 4056-4057
41. Rubio, M.; Suárez, A.; Alvarez, E.; Bianchini, C.; Oberhauser, W.; Peruzzini, M.; Pizzano, A. Organometallics 2007, 26, 6428-6436
42. Arribas, I.; Vargas, S.; Rubio, M.; Suárez, A.; Domene, C.; Alvarez, E.; Pizzano, A. Organometallics 2010, 29, 5791-5804
43. Robert, T.; Abiri, Z.; Wassenaar, J.; Sandee, A. J.; Romanski, S.; Neudörfl, J. -M.; Schmalz, H. -G.; Reek, J. N. H. Organometallics 2010, 29, 478-483
44. Doro, F.; Reek, J. N. H.; van Leeuwen, P. W. N. M. Organometallics 2010, 29, 4440-4447
45. Noonan, G. M.; Fuentes, J. A.; Cobley, C. J.; Clarke, M. L. Angew. Chem., Int. Ed. 2012, 51, 2477-2480
46. Ewalds, R.; Eggeling, E. B.; Hewat, A. C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Chem.-Eur. J. 2000, 6, 1496-1504
47. Wassenaar, J.; Reek, J. N. H. Dalton Trans. 2007, 3750-3753
48. Wassenaar, J.; de Bruin, B.; Reek, J. N. H. Organometallics 2010, 29, 2767-2776
49. Yan, Y.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 7198-7202
50. Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B.; Zhang, X. Chem.-Eur. J. 2010, 16, 871-877
51. Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng., W.; Rand, C. L.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665-2668
52. Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 8671-8676
53. Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047-4050
54. Kawabata, Y.; Hayashi, T.; Ogata, I. J. Chem. Soc., Chem. Commun. 1979, 462-463
55. Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506
56. Petocz, G.; Berente, Z.; Kegl, T.; Kollar, L. J. Organomet. Chem. 2004, 689, 1188-1193
57. Casey., C. P.; Martins, S. C.; Fagan, M. A. J. Am. Chem. Soc. 2004, 126, 5585-5592
58. van der Vlugt, J. I.; van Duren, R.; Batema, G. D.; den Heeten, R.; Meetsma, A.; Fraanje, J.; Goubitz, K.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 2005, 24, 5377-5382
59. van Duren, R.; Cornelissen, L. J. J. M.; van der Vlugt, J. I.; Huibers, J. P. J; Mills, A. M.; Spek, A. L.; Müller, C.; Vogt, D. Helv. Chim. Acta 2006, 89, 1547-1558
60. van Duren, R.; van der Vlugt, J. I.; Mills, A. M.; Spek, A. L.; Vogt, D. Dalton Trans. 2007, 1053-1059
61. Kistamurthy, D.; Otto, S.; Moss, J. R.; Smith, G. S. Transition Met. Chem. (Dordrecht, Neth.) 2010, 35, 633-637
62. del Rio, I.; van Leeuwen, P. W. N. M.; Claver, C. Can. J. Chem. 2001, 79, 560-565
63. Zhang, M.; Tamiya, J.; Nguyen, L.; Rowbottom, M. W.; Dyck, B.; Vickers, T. D.; Grey, J.; Schwarz, D. A.; Heise, C. E.; Haelewyn, J.; Mistry, M. S.; Goodfellow, V. S. Bioorg. Med. Chem. Lett. 2007, 17, 2535-2539
64. Zhu, G. D. Bioorg. Med. Chem. Lett. 2008, 18, 3955-3958
65. Sharma, R.; Lubell, W. D. J. Org. Chem. 1996, 61, 202-209
66. Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 9630-9631
67. Vietti, D. E. U. S. Patent 4376208, 1983.
68. Polo, A.; Real, J.; Claver, C.; Castillon, S.; Bayon, J. C. J. Chem. Soc., Chem. Commun. 1990, 600-601
69. Polo, A.; Claver, C.; Castillon, S.; Ruiz, A. Organometallics 1992, 11, 3525-3533
70. Horiuchi, T.; Ohta, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. J. Org. Chem. 1997, 62, 4285-4292
71. Dieguez, M.; Pamies, O.; Claver, C. Chem. Commun. 2005, 1221-1223
72. Mazuela, J.; Coll, M.; Pamies, O.; Dieguez, M. J. Org. Chem. 2009, 74, 5440-5445
73. The exact bite-angle of this ligand is not reported, but the ligand is believed to coordinate in a bis-equatorial fashion, see: Gual, A.; Godard, C.; Castillon, S.; Claver, C. Adv. Synth. Catal. 2010, 352, 463-477
74. Nozaki, K.; Sato, N.; Tonomura, Y.; Yasutomi, M.; Takaya, H.; Hiyama, T.; Matsubara, T.; Koga, N. J. Am. Chem. Soc. 1997, 119, 12779-12795
75. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2770
76. Wassenaar, J.; van Zutphen, S.; Mora, G.; Le Floch, P; Siegler, M.; Spek, A. L.; Reek, J. N. H. Organometallics 2009, 28, 2724-2734
77. Wassenaar, J.; Kuil, M.; Reek, J. N. H. Adv. Synth. Catal. 2008, 350, 1610-1614
78. Wassenaar, J.; Reek, J. N. H. J. Org. Chem. 2009, 74, 8403-8406
79. Wassenaar, J.; Kuil, M.; Lutz, M.; Spek, A. L.; Reek, J. N. H. Chem.-Eur. J. 2010, 16, 6509-6517
80. Wassenaar, J.; Jansen, E.; van Zeist, W. -J.; Bickelhaupt, F. M.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Nat. Chem. 2010, 2, 417-421
81. Wassenaar, J.; de Bruin, B.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H.; van der Vlugt, J. I. Chem. Commun. 2010, 46, 1432-1434
82. Wassenaar, J.; Siegler, M. A.; Spek, A. L.; de Bruin, B.; Reek, J. N. H.; van der Vlugt, J. I. Inorg. Chem. 2010, 49, 6495-6508
83. Smith, C. R.; RajanBabu, T. V. Org. Lett. 2008, 10, 1657-1659
84. Bellini, R.; Chikkali, S. H.; Berthon-Gelloz, G.; Reek, J. N. H. Angew. Chem., Int. Ed. 2011, 50, 7342-7345
85. Gadzikwa, T.; Bellini, R.; Dekker, H. L.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 2860-2863
86. For a preliminary communication, see: Chikkali, S. H.; Bellini, R.; Berthon-Gelloz, G.; van der Vlugt, J. I.; de Bruin, B.; Reek, J. N. H. Chem. Commun. 2010, 46, 1244-1246
87. Zuidema, E.; Goudriaan, P. E.; Swennenhuis, B. H. G.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. Organometallics 2010, 29, 1210-1221
88. Catalytic tetrazole addition has been previously reported for the preparation of analogous bulky diphosphonites, see: van der Vlugt, J. I.; Hewat, A. C.; Neto, S.; Sablong, R.; Mills, A. M.; Spek, A. L.; Müller, C.; Vogt, D. Adv. Synth. Catal. 2004, 346, 993-1003
89. Evans, D.; Osborn, J. A.; Wilkinson, G. J. J. Chem. Soc. A 1968, 3133-3142
90. Brown, C. K.; Wilkinson, G. J. J. Chem. Soc. A 1970, 2753-2764
91. Yagupsky, G.; Brown, C. K.; Wilkinson, G. J. J. Chem. Soc. A 1970, 1392-1401
92. Casey, C. P.; Whiteker, G. T. Isr. J. Chem. 1990, 30, 290
93. Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A., Jr.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535-5543
94. Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817-11825
95. Dierkes, P.; van Leeuwen, P. W. N. M. Dalton Trans. 1999, 1519-1529
96. Molina, D. A. C.; Casey, C. P.; Müller, I.; Nozaki, K.; Jäkel, C. Organometallics 2010, 29, 3362-3367
97. van der Vlugt, J. I.; Sablong, R.; Magusin, P. C. M. M.; Mills, A. M.; Spek, A.; Vogt, D. Organometallics 2004, 23, 3177-3183
98. During the preparation of this manuscript, a communication appeared reporting 91% ee (7 / 8 = 15:1) from the AHF of 6, see: McDonald, R. I.; Wong, G. W.; Neupane, R. P.; Stahl, S. S.; Landis, C. R. J. Am. Chem. Soc. 2010, 132, 14027-14029
99. Sharma, R.; Lubell, W. D. C. J. Org. Chem. 1996, 61, 202-209
100. Letourneau, J. J.; Paradkar, V.; Ohlmeyer, M. H. J.; Dillard, L. W.; Baldwin, J. J.; Riviello, C. M.; Wang, A.; Rong, W. U. S. Patent 2005222203, 2005.
101. Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas J. Am. Chem. Soc. 2006, 128, 9630-9631
102. Armstrong, A.; Bhonoah, Y.; White, A. J. P. J. Org. Chem. 2009, 74, 5041-5048
103. Min, J. Z.; Toyoóka, T.; Kato, M.; Fukushima, T. Biomed. Chromatogr. 2005, 19, 43-50
104. Blanchet, J.; Pouliquen, M.; Lasne, M. C.; Rouden, J. Tetrahedron Lett. 2007, 48, 5727-5730
105. Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. J. Org. Chem. 1997, 62, 5215-5218
106. Asymmetric hydroformylation from prochiral alkenes to enable the preparation of amino-acids is poorly explored to date: Farwick, A.; Helmchen, G. Adv. Synth. Catal. 2010, 352, 1023-1032
107. Dobbs, A. P.; Voyle, M.; Whittall, N. Synlett. 1999, 1594-1596
108. Kuppert, D.; Sander, J.; Roth, C.; Wörle, M.; Weyhermüller, T.; Reiss, G. J.; Schilde, U.; Müller, I.; Hegetschweiler, K. Eur. J. Inorg. Chem. 2001, 2525-2542