Asymmetric diels-alder and ficini reactions with alkylidene β-ketoesters catalyzed by chiral ruthenium PNNP complexes: Mechanistic insight

Journal of the American Chemical Society

Volumn 134, Issue 2, 2012, Pages 1331-1343

  Schotes, Christoph ^a   Althaus, Martin ^a   Aardoom, Raphael ^a   Mezzetti, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENES; ASYMMETRIC INDUCTION; CHELATING LIGANDS; CYCLOADDITION REACTION; DIASTEREOISOMERS; DICATIONIC COMPLEXES; DIELS-ALDER; DIELS-ALDER ADDUCT; ENANTIOSELECTION; ENOLATES; ESTER GROUPS; HYDRIDE ABSTRACTION; KETOESTER; ROOM TEMPERATURE; STOICHIOMETRIC REACTION; X-RAY STUDIES;

ABSTRACTING; BUTADIENE; CHLORINE COMPOUNDS; COLUMN CHROMATOGRAPHY; HYDRIDES; LIGANDS; OLEFINS; RUTHENIUM; RUTHENIUM COMPOUNDS;

CYCLOADDITION;

1,3 BUTADIENE DERIVATIVE; ALKYL GROUP; AMIDE; CHELATING AGENT; ESTER DERIVATIVE; LIGAND; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; FICINI REACTION; ROOM TEMPERATURE; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 84855959241     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210372u     Document Type: Article

References (102)

1. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650
2. Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds., Springer: Heidelberg, 1999; Vol. 3, pp 1178-1235.
3. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
4. Kobayashi, S.; Jørgensen, K. A. Cycloaddition Reactions in Organic Synthesis; Wiley: Weinheim, 2001.
5. Da, H.; Ding, H. In Handbook of Cyclization Reactions; Ma, S., Ed.; Wiley: Weinheim, 2009; Vol. 1, pp 1-57.
6. Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. 3, p 1229-1230.
7. Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992
8. Honda, Y.; Date, T.; Hiramatsu, H.; Yamauchi, M. Chem. Commun. 1997, 1411
9. Yamauchi, M.; Aoki, T.; Li, M. Z.; Honda, Y. Tetrahedron: Asymmetry 2001, 12, 3113
10. Marx, J. N.; Cox, J. H.; Norman, L. R. J. Org. Chem. 1972, 37, 4489
11. Liu, H. J.; Ngooi, T. K.; Browne, E. N. C. Can. J. Chem. 1988, 66, 3143
12. For instance, the reaction of 2-ethoxycarbonyl-2-cyclohexen-1-one with 1-methylbuta-1,3-diene has been carried out with the stoichiometric activation of the diene by a cobalt complex in the presence of a large excess (4 equiv) of the dienophile over 3 days in refluxing THF and subsequent cleavage of the cobalt complex from the Diels-Alder product, see: Richardson, B. M.; Welker, M. E. J. Org. Chem. 1997, 62, 1299
13. Shizuka, M.; Snapper, M. Angew. Chem., Int. Ed. 2008, 47, 5049
14. Piovesana, S.; Schietroma, D. M. S.; Tulli, L. G.; Monaco, M. R.; Bella, M. Chem. Commun. 2010, 46, 5160
15. Chapdelaine, D.; Belzile, J.; Deslongchamps, P. J. Org. Chem. 2002, 67, 5669
16. Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921
17. Li, W.; Liu, X.; Zhou, X.; Lee, C.-S. Org. Lett. 2010, 12, 548
18. Mezzetti, A. Dalton Trans. 2010, 7851
19. Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087
20. Santoro, F.; Althaus, M.; Bonaccorsi, C.; Gischig, S.; Mezzetti, A. Organometallics 2008, 27, 3866
21. Althaus, M.; Bonaccorsi, C.; Mezzetti, A.; Santoro, F. Organometallics 2006, 25, 3108
22. Bonaccorsi, C.; Althaus, M.; Becker, C.; Togni, A.; Mezzetti, A. Pure Appl. Chem. 2006, 78, 391
23. Toullec, P. Y.; Bonaccorsi, C.; Mezzetti, A.; Togni, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5810
24. Althaus, M.; Becker, C.; Togni, A.; Mezzetti, A. Organometallics 2007, 26, 5902
25. Schotes, C.; Mezzetti, A. J. Am. Chem. Soc. 2010, 132, 3652
26. Schotes, C.; Mezzetti, A. Chimia 2011, 65 (4) 231
27. Schotes, C.; Mezzetti, A. Angew. Chem., Int. Ed. 2011, 50, 3072
28. Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994
29. Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134
30. Janka, M.; He, W.; Frontier, A. J.; Flaschenriem, C.; Eisenberg, R. Tetrahedron 2005, 61, 6193
31. Janka, M.; He, W.; Haedicke, I. E.; Fronczek, F. R.; Frontier, A. J.; Eisenberg, R. J. Am. Chem. Soc. 2006, 128, 5312
32. Kakkonen, H. J.; Pursiainen, J.; Pakkanen, T. A.; Ahlgrén, M.; Iiskola, E. J. Organomet. Chem. 1993, 453, 175
33. Wehrli, F. W.; Marchand, A. P.; Wehrli, S. Interpretation of Carbon-13 NMR Spectra, 2 nd ed.; Wiley: Chichester, 1988; pp 34-38.
34. Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094
35. Cheng, T.-Y.; Szalda, D. J.; Zhang, J.; Bullock, R. M. Inorg. Chem. 2006, 45, 4712
36. Gomberg, M. J. Am. Chem. Soc. 1900, 22, 757
37. Jung, M. E.; Brown, R. W. Tetrahedron Lett. 1978, 31, 2771
38. Jung, M. E.; Pan, Y.-G. J. Org. Chem. 1977, 42, 3961
39. Weng, W.; Chen, C.-H.; Foxman, B. M.; Ozerov, O. V. Organometallics 2007, 26, 3315
40. O'Connor, E. J.; Kobayashi, M.; Floss, H. G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 4837
41. Tam, W.; Lin, G. Y.; Wong, W. K.; Kiel, W. A.; Wong, V. K.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 141
42. Kiel, W. A.; Lin, G.-Y.; Gladysz, J. A. J. Am. Chem. Soc. 1980, 102, 3299
43. Carter, C. A. G.; Casty, G. L.; Stryker, J. M. Synlett 2001, 1046
44. Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar, H. S. J. Org. Chem. 1981, 46, 2920
45. Baker, R.; Selwood, D. L.; Swain, C. J.; Webster, N. M. H. J. Chem. Soc., Perkin Trans. 1 1988, 3, 471
46. Schultz, A. G.; Holoboski, M. A. Tetrahedron Lett. 1993, 34, 3021
47. Chou, H.-H.; Hsieh, M.-T.; Liu, H.-J.; Ly, T. W.; Wu, H.-M.; Wu, Y.-K. Org. Lett. 2009, 11, 1673
48. Nomenclature of Inorganic Chemistry: IUPAC Recommendations 2005; Connelly, N. G.; Hartshorn, R. M.; Damhus, T.; Hutton, A. T., Eds.; RSC Publishing: Cambridge, 2005; pp 174-199.
49. Sloan, T. E. In Topics in Inorganic and Organometallic Stereochemistry; Geoffroy, G. L., Ed.; Topics in Sterochemistry; Wiley: New York, 1981; Vol. 12, pp 1-36.
50. Von Zelevsky, A. Stereochemistry of Coordination Compounds; Wiley: Chichester, 1996.
51. Knof, U.; von Zelevsky, A. Angew. Chem., Int. Ed. 1999, 38, 302-322
52. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity, 4 th ed.; Harper Collins College Publishers: New York, 1993; pp A-30.
53. Fleming, I. Molecular Orbitals and Organic Chemical Reactions, Student ed., 1 st ed.; John Wiley & Sons Ltd.: Chichester, 2009; pp 235-238.
54. Ohwada, T. In Topics in Current Chemistry, Inagaki, S., Ed.; Springer: Berlin/Heidelberg, 2009; Vol. 289, pp 161-171.
55. Schotes, C.; Mezzetti, A. J. Org. Chem. 2011, 76, 5862
56. Trost, B. M.; Jiang, C. Synthesis 2006, 369
57. Yeung, Y. Y.; Chein, R. J.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 10346
58. Canales, E.; Corey, E. J. Org. Lett. 2008, 10, 3271
59. Vicker, N.; Lawrence, H.; Allan, G.; Bubert, C.; Smith, A.; Tutill, H.; Purohit, A.; Day, J.; Mahon, M.; Reed, M.; Potter, B. ChemMedChem 2006, 1, 464
60. Fischer, D. S.; Woo, L. W. L.; Mahon, M. F.; Purohit, A.; Reed, M. J.; Potter, B. V. L Bioorg. Med. Chem. 2003, 11, 1685
61. Labrie, F. Mol. Cell. Endocrinol. 1991, 78, C113
62. MacCarthy-Morrogh, L.; Townsend, P. A.; Purohit, A.; Hejaz, H. A. M.; Potter, B. V. L; Reed, M. J.; Packham, G. Cancer Res. 2000, 60, 5441
63. Biellmann, J. F. Chem. Rev. 2003, 103, 2019
64. Ficini, J.; Krief, A. Tetrahedron Lett. 1969, 10, 1431
65. Ficini, J. Tetrahedron 1976, 32, 1449
66. Evano, A.; Coste, K.; Jouvin Angew. Chem., Int. Ed. 2010, 49, 2840-2859
67. Angew. Chem. 2010, 122, 2902-2921.
68. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
69. Li, H.; Hsung, R. P.; DeKorver, K. A.; Wei, Y. Org. Lett. 2010, 12, 3780
70. Bisswanger, H. Enzyme Kinetics: Principles and Methods, 2 nd ed.; Wiley: Weinheim, 2008; pp 88-119.
71. Corey, E. J.; Loh, T. P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290
72. Paddon-Row, M. N.; Kwan, L. C.H.; Willis, A. C.; Sherburn, M. S. Angew. Chem., Int. Ed. 2008, 47, 7013
73. Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1995, 117, 4435
74. Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 6847
75. Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777
76. Garcia, J. I.; Martinez-Merino, V.; Mayoral, J. A. J. Org. Chem. 1998, 63, 2321
77. Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289
78. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788
79. Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. 3, p 1211.
80. Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. R. J. Org. Chem. 1997, 62, 6454
81. Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-I.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074
82. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481
83. Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Chem. Commun. 1997, 2347
84. Kündig, E. P.; Bourdin, B.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856
85. Rickerby, J.; Vallet, M.; Bernardinelli, G.; Viton, F.; Kündig, E. P. Chem.-Eur. J. 2007, 13, 3354
86. Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; López-Ram de Víu, M. P.; Oro, L. A.; Vega, C.; Viguri, F. Chem. Commun. 1997, 2351
87. Faller, J. W.; Patel, B. P.; Albrizzio, M. A.; Curtis, M. Organometallics 1999, 18, 3096
88. Basolo, F.; Pearson, R. G. Mechanisms of Inorganic Reactions, 3 rd ed.; Wiley: New York, 1963; pp 108-111.
89. Spees, S. T.; Perumareddi, J. R.; Adamson, A. W. J. Am. Chem. Soc. 1968, 90, 6626
90. Schotes, C.; Ranocchiari, M.; Mezzetti, A. Organometallics 2011, 30, 3596
91. Becker, C.; Kieltsch, I.; Broggini, D.; Mezzetti, A. Inorg. Chem. 2003, 42, 8417
92. Mezzetti, A.; Becker, C. Helv. Chim. Acta 2002, 85, 2686
93. Pauling, L. The Nature of the Chemical Bond, 3 rd ed.; Cornell University Press: New York, 1960; pp 172-174.
94. Bonaccorsi, C.; Santoro, F.; Gischig, S.; Mezzetti, A. Organometallics 2006, 25, 2002
95. Bonaccorsi, C.; Bachmann, S.; Mezzetti, A. Tetrahedron: Asymmetry 2003, 14, 845
96. Stoop, R. M.; Bachmann, S.; Valentini, M.; Mezzetti, A. Organometallics 2000, 19, 4117
97. Gao, J. X.; Xu, P. P.; Yi, X. D.; Yang, C. B.; Zhang, H.; Cheng, S. H.; Wan, H. L.; Tsai, K R.; Ikariya, T. J. Mol. Catal. A: Chem. 1999, 147, 105
98. Sui-Seng, C.; Haque, F. N.; Hadzovic, A.; Pütz, A. M.; Reuss, V.; Meyer, N.; Lough, A. J.; Zimmer-De Iuliis, M.; Morris, R. H. Inorg. Chem. 2009, 48, 735
99. Zhang, H.; Yang, C. B.; Li, Y. Y.; Donga, Z. R.; Gao, J. X.; Nakamura, H.; Murata, K.; Ikariya, T. Chem. Commun. 2003, 142
100. Masson-Szymczak, A.; Riant, O.; Gref, A.; Kagan, H. B. J. Organomet. Chem. 1996, 511, 193
101. Song, J. H.; Cho, D. J.; Jeon, S. J.; Kim, Y.-H.; Kim, T. J.; Jeong, J. H. Inorg. Chem. 1999, 38, 893
102. Ranocchiari, M.; Mezzetti, A. Organometallics 2009, 28, 1286