Up to 96% enantioselectivities in the hydrogenation of fluorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified palladium catalyst

Advanced Synthesis and Catalysis

Volumn 350, Issue 17, 2008, Pages 2804-2814

  Szollosi, György ^a   Hermán, Beáta ^a,b   Felföldi, Károly ^a   Fülöp, Ferenc ^a,b   Bartók, Mihály ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Asymmetric hydrogenation; Cinchonidine; Diphenylpropenoic acid; Fluorine; Palladium; Substituent effect

Indexed keywords

EID: 56749091751     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800458     Document Type: Article

References (102)

1. a) E. Francotte, W. Lindner (Eds.), Chirality in Drug Research, Wiley-VCH, Weinheim, 2006;
2. b) M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem. 2004, 116, 806-843;
3. Angew. Chem. Int. Ed. 2004, 43, 788-824.
4. a) T. Ohkuma, M. Kitamura, R. Noyori, in: Catalytic Asymmetric Synthesis 2nd edn., (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, Chapt. 1, pp 1-110;
5. b) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151;
6. c) H.-U. Blaser, E. Schmidt (Eds.), Asymmetric Catalysis on Industrial Scale. Challenges, Approaches and Solutions, Wiley-VCH, Weinheim, 2004;
7. d) H.-U. Blaser, B. Pugin, F. Spindler, J. Mol. Catal. A: Chem. 2005, 231, 1-20.
8. a) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069;
9. b) C. Jäkel, R. Paciello, Chem. Rev. 2006, 106, 2912-2942;
10. c) J. A. F. Boogers, U. Felfer, M. Kotthaus, G. Steinbauer, A. H. M. de Vries, J. G. de Vries, Org. Proc. Res. Dev. 2007, 11, 585-591;
11. d) H.-U. Blaser, B. Pugin, F. Spindler, M. Thommen, Acc. Chem. Res. 2007, 40, 1240-1250;
12. e) A. J. Minnaard, B. L. Feringa, L. Lefort, J. G. de Vries, Acc. Chem. Res. 2007, 40, 1267-1277.
13. a) D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs (Eds.), Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000;
14. b) M. Studer, H.-U. Blaser, C. Exner, Adv. Synth. Catal. 2003, 345, 45-65;
15. c) D. Yu. Murzin, P. Mäki-Arvela, E. Toukoniitty, T. Salmi, Catal. Rev. Sci. Eng. 2005, 47, 175-256;
16. d) M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. 2006, 118, 4850-4881;
17. Angew. Chem. Int. Ed. 2006, 45, 4732-4762;
18. e) T. Mallat, E. Orglmeister, A. Baiker, Chem. Rev. 2007, 107, 4863-4890.
19. a) A. Tai, T. Kikukawa, T. Sugimura, Y. Inoue, T. Osawa, A. Fujii, J. Chem. Soc. Chem. Commun. 1991, 795-796;
20. b) T. Sugimura, S. Nakagawa, A. Tai, Bull. Chem. Soc. Jpn. 2002, 75, 355-363;
21. c) T. Osawa, T. Harada, O. Takayasu, Curr. Org. Chem. 2006, 10, 1513-1531.
22. a) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc. Jpn. 1979, 1118-1120;
23. b) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc. Jpn. 1980, 670-672;
24. c) M. von Arx, T. Mallat, A. Baiker, Top. Catal. 2002, 19, 75-87;
25. d) C. Exner, A. Pfaltz, M. Studer, H.-U. Blaser, Adv. Synth. Catal. 2003, 345, 1253-1260;
26. e) M. Bartók, Curr. Org. Chem. 2006, 10, 1533-1567.
27. a) J. R. G. Perez, J. Malthête, J. Jacques, C. R. Acad. Sc. Paris Série II 1985, 300, 169-172;
28. b) M. Bartók, Gy. Wittmann, Gy. Göndös, G. V. Smith, J. Org. Chem. 1987, 52, 1139-1141;
29. c) Y. Nitta, Y. Ueda, T. Imanaka, Chem. Lett. 1994, 23, 1095-1098;
30. d) Y. Nitta, K. Kobiro, Chem. Lett. 1996, 25, 897-898;
31. e) T. J. Hall, P. Johnston, W. A. H. Vermeer, S. R. Watson, P. B. Wells, Stud. Surf. Sci. Catal. 1996, 101, 221-230;
32. f) K. Borszeky, T. Mallat, A. Baiker, Catal. Lett. 1996, 41, 199-202;
33. g) K. Borszeky, T. Mallat, A. Baiker, Tetrahedron: Asymmetry 1997, 8, 3745-3753;
34. h) K. Borszeky, T. Bürgi, Z. Zhaohui, T. Mallat, A. Baiker, J. Catal. 1999, 187, 160-166;
35. i) M. Maris, W.-R. Huck, T. Mallat, A. Baiker, J. Catal. 2003, 219, 52-58;
36. j) A. Solladi-Cavallo, F. Hoernel, M. Schmitt, F. Garin, J. Mol. Catal. A: Chem. 2003, 195, 181-188;
37. k) Y. Nitta, T. Kubota, Y. Okamoto, J. Mol. Catal. A: Chem. 2004, 212, 155-159;
38. l) M. Casagrande, S. Franceschini, M. Lenarda, O. Piccolo, A. Vaccari, J. Mol. Catal. A: Chem. 2006, 246, 263-267;
39. m) A. Tungler, É. Sípos, V. Háda, Curr. Org. Chem. 2006, 10, 1569-1583.
40. a) I. Kun, B. Török, K. Felföldi, M. Bartók, Appl. Catal. A: Gen. 2000, 203, 71-79;
41. b) Gy. Szocombining double acute accentllocombining double acute accentsi, S. Niwa, T. Hanaoka, F. Mizukami, J. Mol. Catal. A: Chem. 2005, 230, 91-95;
42. c) Gy. Szocombining double acute accentllocombining double acute accentsi, T. Hanaoka, S. Niwa, F. Mizukami, M. Bartók, J. Catal. 2005, 231, 480-483;
43. d) K. Szocombining double acute accentri, Gy. Szocombining double acute accentllocombining double acute accentsi, K. Felföldi, M. Bartók, React. Kinet. Catal. Lett. 2005, 84, 151-156;
44. e) Gy. Szocombining double acute accentllocombining double acute accentsi, E. Szabó, M. Bartók, Adv. Synth. Catal. 2007, 349, 405-410;
45. f) Gy. Szocombining double acute accentllocombining double acute accentsi, K. Balázsik, M. Bartók, Appl. Catal. A: Gen. 2007, 319, 193-201;
46. g) B. Hermán, Gy. Szocombining double acute accentllocombining double acute accentsi, F. Fülöp, M. Bartók, Appl. Catal. A: Gen. 2007, 331, 39-43;
47. h) Gy. Szocombining double acute accentllocombining double acute accentsi, Magy. Kém. Foly. 2007, 113, 146-153;
48. i) Gy. Szocombining double acute accentllocombining double acute accentsi, K. Szocombining double acute accentri, M. Bartók, J. Catal. 2008, 256, 349-352;
49. j) K. Szocombining double acute accentri, Gy. Szovllocombining double acute accentsi, M. Bartók, New J. Chem. 2008, 32, 1354-1358.
50. a) W.-R. Huck, T. Mallat, A. Baiker, J. Catal. 2000, 193, 1-4;
51. b) W.-R. Huck, T. Bürgi, T. Mallat, A. Baiker, J. Catal. 2001, 200, 171-180;
52. c) W.-R. Huck, T. Mallat, A. Baiker, New J. Chem. 2002, 26, 6-8;
53. d) W.-R. Huck, T. Bürgi, T. Mallat, A. Baiker, J. Catal. 2003, 219, 41-51;
54. e) W.-R. Huck, T. Mallat, A. Baiker, Adv. Synth. Catal. 2003, 345, 255-260.
55. a) Y. Nitta, Chem. Lett. 1999, 28, 635-636;
56. b) Y. Nitta, Top. Catal. 2000, 13, 179-185;
57. c) T. Sugimura, J. Watanabe, T. Okuyama, Y. Nitta, Tetrahedron: Asymmetry 2005, 16, 1573-1575;
58. d) Y. Nitta, J. Watanabe, T. Okuyama, T. Sugimura, J. Catal. 2005, 236, 164-167;
59. e) T. Sugimura, J. Watanabe, T. Uchida, Y. Nitta, T. Okuyama, Catal. Lett. 2006, 112, 27-30.
60. Gy. Szocombining double acute accentllocombining double acute accentsi, B. Hermán, K. Felföldi, F. Fülöp, M. Bartók, J. Mol. Catal. A: Chem. 2008, 290, 54-59.
61. A. P. G. Kieboom, H. van Bekkum, J. Catal. 1972, 25, 342-349.
62. a) J. A. K. Howard, V. J. Hoy, D. O Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613-12622;
63. b) J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89-98;
64. c) A. Vargas, F. Hoxha, N. Bonalumi, T. Mallat, A. Baiker, J. Catal. 2006, 240, 203-212.
65. a) K. Mikami, Y. Itoh, M. Yamanaka, Chem. Rev. 2004, 104, 1-16;
66. b) J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119-6146;
67. c) H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147-1155;
68. d) M. Oestreich, Angew. Chem. 2005, 117, 2376-2379;
69. Angew. Chem. Int. Ed. 2005, 44, 2324-2327.
70. a) T. Ohkuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1998, 120, 13529-13529;
71. b) Y. Kuroki, D. Asada, K. Iseki, Tetrahedron Lett. 2000, 41, 9853-9858;
72. c) Y. Kuroki, Y. Sakamaki, K. Iseki, Org. Lett. 2001, 3, 457-459;
73. d) M. Berthod, G. Mignani, M. Lemaire, J. Mol. Catal. A: Chem. 2005, 233, 105-110.
74. a) T. Mallat, M. Bodmer, A. Baiker, Catal. Lett. 1997, 44, 95-99;
75. b) B. Török, K. Balázsik, Gy. Szöllocombining double acute accentsi, K. Felföldi, M. Bartók, Chirality 1999, 11, 470-474;
76. c) K. Balázsik, B. Török, K. Felföldi, M. Bartók, Ultrasonics Sonochem. 1999, 5, 149-155;
77. d) M. von Arx, T. Mallat, A. Baiker, J. Catal. 2000, 193, 161-164;
78. e) M. von Arx, T. Mallat, A. Baiker, Tetrahedron: Asymmetry 2001, 12, 3089-3094;
79. f) M. von Arx, T. Mallat, A. Baiker, Catal. Lett. 2002, 78, 267-271;
80. g) R. Hess, S. Diezi, T. Mallat, A. Baiker, Tetrahedron: Asymmetry 2004, 15, 251-257;
81. h) T. Varga, K. Felföldi, P. Forgó, M. Bartók, J. Mol. Catal. A: Chem. 2004, 216, 181-187;
82. i) S. Diezi, M. Hess, E. Orglmeister, T. Mallat, A. Baiker, Catal. Lett. 2005, 102, 121-125;
83. j) S. Diezi, M. Hess, E. Orglmeister, T. Mallat, A. Baiker, Catal. Lett. 2005, 239, 49-56.
84. M. von Arx, T. Mallat, A. Baiker, Angew. Chem. 2001, 113, 2369-2372;
85. Angew. Chem. Int. Ed. 2001, 40, 2302-2305.
86. a) K. Szocombining double acute accentri, Gy. Szocombining double acute accentllocombining double acute accentsi, M. Bartók, Adv. Synth. Catal. 2006, 348, 515-522;
87. b) K. Szocombining double acute accentri, Gy. Szocombining double acute accentllocombining double acute accentsi, M. Bartók, J. Catal. 2006, 244, 255-259.
88. Gy. Szocombining double acute accentllocombining double acute accentsi, T. Varga, K. Felföldi, Sz. Cserényi, M. Bartók, Catal. Commun. 2008, 9, 421-424.
89. N. Bonalumi, A. Vargas, D. Ferri, A. Baiker, J. Phys. Chem. B 2006, 110, 9956-9965.
90. a) I. Pálinkó, A. Burrichter, G. Rasul, B. Török, G. K. S. Prakash, G. A. Olah, J. Chem. Soc. Perkin Trans. 2 1998, 379-385;
91. b) J. T. Kiss, K. Felföldi, I. Hannus, I. Pálinkó, J. Mol. Struct. 2001, 565-566, 463-468;
92. c) T. M. Babar, N. H. Rama, G. Qadeer, G. S. Khan, W.-Y. Wong, Acta Crystallogr. Sect. E 2006, E62, o4082-o4083.
93. a) R. W. Taft Jr. , J. Am. Chem. Soc. 1957, 79, 1045-1049;
94. b) R. W. Taft Jr. , J. Phys. Chem. 1960, 64, 1805-1815;
95. c) J. Hine, J. Am. Chem. Soc. 1960, 82, 4877-4880.
96. R. Hess, T. Mallat, A. Baiker, J. Catal. 2003, 218, 453-456.
97. S. E. Boiadjiev, D. A. Lightner, J. Phys. Org. Chem. 1999, 12, 751-757.
98. a) S. Lavoie, M.-A. Laliberté, I. Temprano, P. H. McBreen, J. Am. Chem. Soc. 2006, 128, 7588-7593;
99. b) M.-A. Laliberté, S. Lavoie, B. Hammer, G. Mahieu, P. H. McBreen, J. Am. Chem. Soc. 2008, 130, 5386-5387.
100. R. Fuchs, J. J. Bloomfield, J. Org. Chem. 1966, 31, 3423-3425.
101. K. Bowden, D. C. Parkin, Can. J. Chem. 1968, 46, 3909-3914.
102. K. Felföldi, M. Sutyinszky, N. Nagy, I. Pálinkó, Synth. Commun. 2000, 30, 1543-1553.