Theoretical insights into enantioselective catalysis: The mechanism of the Kharasch-Sosnovsky reaction

Chemistry - A European Journal

Volumn 14, Issue 30, 2008, Pages 9274-9285

  Mayoral, José Antonio ^a   Rodríguez Rodríguez, Sergio ^a   Salvatella, Luis ^a  

^a CSIC   (Spain)

Author keywords

Copper; Density functional calculations; Homogeneous catalysis; Oxidation; Reaction mechanisms

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CATALYSIS; CHEMICAL REACTIONS; COPPER; ENANTIOSELECTIVITY; HYDROGEN; ION EXCHANGE; LIGANDS; OLEFINS; REACTION KINETICS;

ALLYLIC HYDROGENS; BISOXAZOLINE; CATALYST COMPLEXES; CHIRAL REACTIONS; CONSISTENT; COPPER COMPLEXES; CYCLOHEXENE; DENSITY-FUNCTIONAL CALCULATIONS; ENANTIOSELECTIVE CATALYSES; HOMOGENEOUS CATALYSIS; LABELED SUBSTRATES; LIGAND EXCHANGES; LIMITING STEPS; MECHANISTIC PATHWAYS; OXIDATIVE ADDITION REACTIONS; REACTION MECHANISMS; REACTION PRODUCTS; REDUCTIVE ELIMINATIONS; SCRAMBLING;

COPPER COMPOUNDS;

EID: 55049133734     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800638     Document Type: Article

References (104)

1. M. B. Andrus, J. C. Lashley, Tetrahedron 2002, 55, 845-866.
2. a) J. Le Paih, G. Schlingloff, C. Bolm in Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, Vol. 2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 256-266;
3. b) X-C. Frison, J. Legros, C. Bolm in Handbook of CH Transformations (Ed.: O. Dyker), Wiley-VCH, Weinheim, 2005, pp. 445-454;
4. c) T. Punniyamurthy, L. Rout, Coord. Chem. Rev. 2008, 252, 134-154.
5. A. J. Pearson, Y.-S. Chen, G. R. Han, S-Y. Hsu, T. Ray, J. Chem. Soc. Perkin Trans. 11985, 267-270.
6. G. Sekar, A. DattaGupta, V. K. Singh, J. Org. Chem. 1998, 63, 2961-2967.
7. J. Eames, M. Watkinson, Angew. Chem. 2001, 113, 3679-3683;
8. Angew. Chem. Int. Ed. 2001, 40, 3567-3571.
9. a) S. L. Schreiber, R. E. Claus, J. Reagan, Tetrahedron Lett. 1982, 23, 3867-3870;
10. b) R. Hayes, T. W. Wallace, Tetrahedron Lett. 1990, 31, 3355-3356.
11. a) H. A. McManus, P.J. Guiry, Chem. Rev. 2004, 104, 4151-4202;
12. b) G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561-3651.
13. X.-S. Wang, H. Zhao, Y.-H. Li, R.-G. Xiong, X.-Z. You, Top. Catal 2005, 55, 43-61.
14. K. Smith, C. D. Hupp, K. L. Allen, G. A. Slough, Organometallics 2005, 24, 1747-1755.
15. S. H. Bertz, S. Cope, M. Murphy, C. A. Ogle, B. J. Taylor, J. Am. Chem. Soc. 2007, 129, 7208-7209.
16. J. K. Kochi, Tetrahedron 1962, 18, 483-497.
17. A. L. J. Beckwith, A. A. Zavitsas, J. Am. Chem. Soc. 1986, 108, 8230-8234.
18. M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1994, 59, 214-216.
19. D. B. Denney, D. Z. Denney, G. Feig, Tetrahedron Lett. 1959, 19-23.
20. a) N. V. Gorbunova, A. P. Purmal', Yu. I. Skurlatov, Zh. Fiz. Khim. 1975, 49, 1995-1999;
21. N. V. Gorbunova, A.P. Purmal', Y. I. Skurlatov, Russ. J. Phys. Chem. 1975, 49, 1169-1171;
22. b) N. V. Gorbunova, Yu. I. Skurlatov, Zh. Fiz. Khim. 1977, 57, 875-879;
23. N. V. Gorbunova, Y. I. Skurlatov, Russ. J. Phys. Chem. 1977, 57, 513-515;
24. c) G. R. A. Xohnson, N. B. Nazhat, J. Am. Chem. Soc. 1987, 109, 1990-1994;
25. d) G. R. A. Johnson, J. B. Nazhat, R. A. Saadalla-Nazhat, J. Chem. Soc. Faraday Trans. 1, 1988, 84, 501-510.
26. Yu. Skurlatov, Int. J. Chem. Kinet. 1980, 12, 347-370.
27. Y. Hiraku, S. Kawanishi, Cancer Res. 1996, 16, 1786-1793.
28. G. Speier, V. Fülöp, J. Chem. Soc. Chem. Commun. 1990, 905-906.
29. a) M. A. Lockwood, T. J. Blubaugh, A. M. Collier, S. Lovell, J. M. Mayer, Angew. Chem. 1999, 111, 178-180;
30. Angew. Chem. Int. Ed. 1999, 38, 225-227;
31. b) A. Amine, Z. Atmani, A. E. Hallaoui, M. Giorgi, M. Pierrot, M. Réglier, Bioorg. Med. Chem. Lett. 2002, 12, 57-60.
32. C. Berglund, S.-O. Lawesson, Arkiv Kemi 1963, 20, 225-244.
33. a) H. L. Goering, S.S. Kantner, J. Org. Chem. 1983, 48, 721-724;
34. b) H. L. Goering, V. D. Singleton, Jr., J. Org. Chem. 1983, 48, 1531-1533;
35. c) H. L. Goering, C. C. Tseng, J. Org. Chem. 1983, 48, 3986-3990;
36. d) H. L. Goering, S. S. Kantner, J. Org. Chem. 1984, 49, 422 426;
37. e) C. C. Tseng, S. D. Paisley, H. L. Goering, J. Org. Chem. 1986, 57, 2884-2891;
38. f) J.-E. Bäckvall, E. S. M. Persson, A. Bombrun, J. Org. Chem. 1994, 59, 4126-4130;
39. g) H.L. Goering, C. C. Tseng, J. Org. Chem. 1985, 50, 1597-1599;
40. h) H.-J. Gais, H. Müller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453-2466;
41. i) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989;
42. j) V. Liepins, J.-E. Bäckvall, Org. Lett. 2001, 5, 1861-1864;
43. k) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681;
44. l) J. Norinder, J.-E. Bäckvall, Chem. Eur. J. 2007, 13, 4094-4102;
45. m) J. Norinder, K. Bogár, L. Kanupp, J.-E. Bäckvall, Org. Lett. 2007, 9, 5095-5098.
46. M. Yamanaka, S. Kato, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 6287-6293.
47. J. Norinder, J.-E. Bäckvall, N. Yoshikai, E. Nakamura, Organometallics 2006, 25, 2129-2132.
48. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
49. C. Walling, A. A. Zavitsas, J. Am. Chem. Soc. 1963, 85, 2084-2090.
50. M. Ahlquist, V. V. Fokin, Organometallics 2007, 26, 4389-4391.
51. A. L. Beckwith, G. W. Evans, Proc. Chem. Soc. 1962, 63-64.
52. A. K. Franz, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 949-957.
53. M. B. Andrus, A. B. Argade, X. Chen, M. G. Pamment, Tetrahedron Lett. 1995, 56, 2945-2948.
54. J.-M. Ducéré, A. Goursot, D. Berthomieu, J. Phys. Chem. A 2005, 109, 400-408.
55. a) M. C. Holthausen, M. Mohr, W. Koch, Chem. Phys. Lett. 1995, 240, 245-252;
56. b) A. Luna, M. Alcamí, O. Mo, M. Yáñez, Chem. Phys. Lett. 2000, 320, 129-138;
57. c) G. Vitale, A. B. Valina, H. Huang, R. Amunugama, M. T. Rodgers, J. Phys. Chem. A 2001, 105, 11351-11364.
58. M. Yamanaka, A. Inagaki, E. Nakamura, J. Comput. Chem. 2003, 24, 1401-1409.
59. L. D. Shirtcliff, M. M. Haley, R. Merges, J. Org. Chem. 2007, 72, 2411-2418.
60. a) J. M. Fraile, J. I. García, V. Martínez-Merino, J. A. Mayoral, L. Salvatella, J. Am. Chem. Soc. 2001, 123, 7616-7625;
61. b) M. Itagaki, K. Masumoto, K. Suenobu, Y. Yamamoto, Org. Process Res. Dev. 2006, 10, 245-250.
62. A. Hajra, N. Yoshikai, E. Nakamura, Org. Lett. 2006, 8, 4153-4155.
63. G. Huerta, L. Fomina, J. Mol. Struct. (THEOCHEM) 2006, 761, 107-112.
64. M. A. Celik, M. Yurtsever, N. Ş. Tüzün, F. Ö. Güngör, Ö. Sezer, O. Anaç, Organometallics 2007, 26, 2978-2985.
65. Gaussian03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, X C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
66. T. V. Popova, N. V. Aksenova, Russ. J. Coord. Chem. 2003, 29, 743-765.
67. H. Hu, J. P. Snyder, J. Am. Chem. Soc. 2007, 129, 7210-7211.
68. R. Santo, R. Miyamoto, R. Tanaka, T. Nishioka, K. Sato, K. Toyota, M. Obata, S. Yano, I. Kinoshita, A. Ichimura, Angew. Chem. 2006, 118, 7773-7776;
69. Angew. Chem. Int. Ed. 2006, 45, 7611-7614.
70. a) B. S. Jursic, J. Mol. Struct. (THEOCHEM) 1998, 442, 253-257;
71. b) J. J. M. Wiener, P. Politzer, J. Mol. Struct. (THEOCHEM) 1998, 427, 171-174;
72. c) Y. Feng, L. Liu, J.-T. Wang, H. Huang, Q.-X. Guo, J. Chem. Inf. Comput. Sci. 2003, 43, 2005-2013;
73. d) X.-Q. Yao, X.-J. Hou, H. Jiao, H.-W. Xiang, Y.-W. Li, J. Phys. Chem. A 2003, 107, 9991-9996;
74. e) X. J. Qi, Y. Feng, L. Liu, Q. X. Guo, Chin. J. Chem. 2005, 23, 194-199;
75. f) Y. Fu, X.-Y. Dong, Y.-M. Wang, L. Liu, Q.-X. Guo, Chin. J. Chem. 2005, 23, 474-482.
76. H. Basch, Inorg. Chim. Acta 1996, 252, 265-279.
77. B. G. Johnson, C. A. Gonzales, P. M. W. Gill, J. A. Pople, Chem. Phys. Lett. 1994, 221, 100-108.
78. N. Gomez, E. Hénon, F. Bohr, P. Devolder, J. Phys. Chem. A 2001, 105, 11204-11211.
79. P. C. Wong, D. Griller, J. C. Scaiano, J. Am. Chem. Soc. 1982, 104, 5106-5108.
80. H. Kwart, Acc. Chem. Res. 1982, 15, 401-408.
81. a) G. F. Larson, R. D. Gilliom, J. Am. Chem. Soc. 1975, 97, 3444-3447;
82. b) E. S. Lewis, K. Ogino, J. Am. Chem. Soc. 1976, 98, 2264-2268;
83. c) S. S. Kim, S. Y. Kim, S. S. Ryou, C. S. Lee, K. H. Yoo, J. Org. Chem. 1993, 58, 192-196;
84. d) J. I. Manchester, J. P. Dinnocenzo, L. Higgins, J. P. Jones, J. Am. Chem. Soc. 1997, 119, 5069-5070.
85. H. Kwart, D. A. Benko, M. E. Bromberg, J. Am. Chem. Soc. 1978, 100, 7093-7094.
86. H. J. Shine, J. R. Slagle, J. Am. Chem. Soc. 1959, 81, 6309-6313.
87. a) M. T. Caudle, P. Riggs-Gelasco, A. K. Gelasco, J. E. Penner-Hahn, V.-L. Pecoraro, Inorg. Chem. 1996, 35, 3577-3584;
88. b) A. Bravo, H.-R. Bjørsvik, F. Fontana, L. Liguori, F. Minisci, J. Org. Chem. 1997, 62, 3849-3857.
89. S. Bärsch, D. Schröder, H. Schwarz, Helv. Chim. Acta 2000, 83, 827-835.
90. C. Filliatre, C. Manigand, A. Raharisoa, J.-J. Villenave, Thermochim. Acta 1984, 74, 9-22.
91. F. Löpez, A. J. Minnaard, B. L. Feringa, Acc. Chem. Res. 2007, 40, 179-188.
92. M. Melník, M. Kabeašová, J. Coord. Chem. 2000, 50, 323-338.
93. H. Kwart, M. Brechbiel, W. Miles, L. D. Kwart, J. Org. Chem. 1982, 47, 4524-4528.
94. G. Rothenberg, Y. Sasson, Tetrahedron 1998, 54, 5417-5422.
95. G. Malaisé, S. Ramdeehul, J. A. Osborn, L. Barloy, N. Kyritsakas, R. Graff, Eur. J. Inorg. Chem. 2004, 3987-4001.
96. J. Andraos, J. Phys. Chem. A 2003, 107, 2374-2387.
97. A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831-1834.
98. R. W. Hoffmann, A. Polachowski, Chem. Eur. J. 1998, 4, 1724-1730.
99. P. W. C. Barnard, N. C. Yang, Chem. Ind. 1961, 1573.
100. E. Nakamura, S. Mori, Angew. Chem. 2000, 112, 3902-3924;
101. Angew. Chem. Int. Ed. 2000, 59, 3750-3771.
102. a) I P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337-2364;
103. b) S.-L. Zhang, L. Liu, Y. Fu, Q.-X. Guo, Organometallics 2007, 26, 4546-4554.
104. S. Woodward, Chem. Soc. Rev. 2000, 29, 393-401.