Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands

Chemistry - A European Journal

Volumn 10, Issue 1, 2004, Pages 294-302

  Bøgevig, Anders ^a   Pastor, Isidro M ^a   Adolfsson, Hans ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Amino acids; Amino alcohols; Asymmetric catalysis; Hydrogen transfer; Ruthenium

Indexed keywords

ALCOHOLS; AMINO ACIDS; CATALYSIS; CATALYSTS; REDUCTION; RUTHENIUM; STEREOCHEMISTRY;

ENANTIOSELECTIVITY;

KETONES;

1 PHENYLETHANOL; 2 PROPANOL; ACETOPHENONE; ALANINE DERIVATIVE; ALCOHOL DERIVATIVE; ALKYL GROUP; ALPHA AMINO ACID; DIPEPTIDE; KETONE DERIVATIVE; LIGAND; PARA CYMENE; PEPTIDE DERIVATIVE; PHENYLETHANOLAMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOMER; ENANTIOSELECTIVITY; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION;

EID: 0345827492     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305553     Document Type: Article

References (77)

1. For reviews, see: a) U. Matteoli, P. Frediani, M. Bianchi, C. Botteghi, S. Gladiali, J. Mol. Catal. 1981, 12, 265-319;
2. b) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 1992, 92, 1051-1069;
3. c) J.-E. Bäckvall, R. L. Chowdhury, U. Karlsson, G. Z. Wang in Perspectives in Coordination Chemistry (Eds.: A. F. Williams, C. Floriani, A. E. Merbach), Helvetica Chimica Acta, Basel, Basel., 1992, pp. 463-486;
4. d) C. F. de Graauw, J. A. Peters, H. van Bekkum, J. Huskens, Synthesis 1994, 1007-1017;
5. e) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102;
6. f) M. J. Palmer, M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045-2061;
7. g) J.-E. Bäckvall, J. Organomet. Chem. 2002, 652, 105-111;
8. h) K. Everaere, A. Mortreux, J.-F. Carpentier, Adv. Synth. Catal. 2003, 345, 67-77;
9. i) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151.
10. a) D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240;
11. b) J.-P. Genêt, V. Ratovelomanana-Vidal, C. Pinel, Synlett 1993, 478-480;
12. c) P. Gamez, F. Fache, M. Lemaire, Tetrahedron: Asymmetry 1995, 6, 705-718;
13. d) D. A. Evans, S. G. Nelson, M. R. Gagné, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800-9801;
14. e) Y. Jiang, Q. Jiang, X. Zhang, J. Am. Chem. Soc. 1998, 120, 3817-3818;
15. f) Y. Nishibayashi, I. Takei, S. Uemura, M. Hidai, Organometallics 1999, 18, 2291-2293.
16. a) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563;
17. b) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522;
18. c) D. A. Alonso, D. Guijarro, P. Pinho, O. Temme, P. G. Andersson, J. Org. Chem. 1998, 63, 2749-2751;
19. d) D. A. Alonso, S. J. M. Nordin, P. Roth, T. Tarnai, P. G. Andersson, M. Thommen, U. Pittelkow, J. Org. Chem. 2000, 65, 3116-3122;
20. e) S. J. M. Nordin, P. Roth, T. Tarnai, D. A. Alonso, P. Brandt, P. G. Andersson, Chem. Eur. J. 2001, 7, 1431-1436;
21. f) M. Palmer, T. Walsgrove, M. Wills, J. Org. Chem. 1997, 62, 5226-5228;
22. g) M. Wills, M. Gamble, M. Palmer, A. Smith, J. Studley, J. Kenny, J. Mol. Catal. A 1999, 146, 139-148;
23. h) M. J. Palmer, J. A. Kenny, T. Walsgrove, A. M. Kawamoto, M. Wills, J. Chem. Soc. Perkin Trans. 1 2002, 416-427;
24. i) M. Watanabe, K. Murata, T. Ikariya, J. Org. Chem. 2002, 67, 1712-1715;
25. j) K. Everaere, J.-F. Carpentier, A. Mortreux, M. Bulliard, Tetrahedron: Asymmetry 1998, 9, 2971-2974;
26. k) K. Everaere, J.-F. Carpentier, A. Mortreux, M. Bulliard, Tetrahedron: Asymmetry 1999, 10, 4083-4086;
27. l) K. Everaere, J.-F. Carpentier, A. Mortreux, M. Bulliard, Tetrahedron: Asymmetry 1999, 10, 4663-4666;
28. m) K. Everaere, A. Mortreux, M. Bulliard, J. Brussee, A. van der Gen, G. Nowogrocki, J.-F. Carpentier, Eur. J. Org. Chem. 2001, 275-291;
29. n) K. Everaere, N. Franceschini, A. Mortreux, J.-F. Carpentier, Tetrahedron Lett. 2002, 43, 2569-2571;
30. o) C. Bubert, J. Blacker, S. M. Brown, J. Crosby, S. Fitzjohn, J. P. Muxworthy, T. Thorpe, J. M. J. Williams, Tetrahedron Lett. 2001, 42, 4037-4039;
31. p) Y. Ma, H. Liu, L. Chen, J. Zhu, J. Deng, Org. Lett. 2003, 5, 2103-2106;
32. q) J. Soleimannejad, A. Sisson, C. White, Inorg. Chim. Acta 2003, 352, 121-128;
33. r) M. Aitali, S. Allaoud, A. Karim, C. Meliet, A. Mortreux, Tetrahedron: Asymmetry 2000, 11, 1367-1374;
34. s) B. Mohar, A. Valleix, J.-R. Desmurs, M. Felemez, A. Wagner, C. Mioskowski, Chem. Commun. 2001, 2572-2573;
35. t) D. Šterk, M. S. Stephan, B. Mohar, Tetrahedron: Asymmetry 2002, 13, 2605-2608.
36. a) I. M. Pastor, P. Västilä, H. Adolfsson, Chem. Commun. 2002, 2046-2047;
37. b) I. M. Pastor, P. Västilä, H. Adolfsson, Chem. Eur. J. 2003, 9, 4031-4045.
38. For other examples of amino acid based ligands in the transfer hydrogenation of ketones, see: a) T. Ohta, S. Nakahara, Y. Shigemura, K. Hattori, I. Furokawa, Chem. Lett. 1998, 491-492;
39. b) T. Ohta, S. Nakahara, Y. Shigemura, K. Hattori, I. Furokawa, Appl. Organomet. Chem. 2001, 15, 699-709;
40. c) D. Carmona, F. J. Lahoz, R. Atencio, L. A. Oro, M. P. Lamata, F. Viguri, E. San José, C. Vega, J. Reyes, F. Joó, Á. Kathó, Chem. Eur. J. 1999, 5, 1544-1564;
41. d) Á. Kathó, D. Carmona, F. Viguri, C. D. Remacha, J. Kovács, F. Joó, L. A. Oro, J. Organomet. Chem. 2000, 593-594, 299-306;
42. e) D. Carmona, M. P. Lamata, F. Viguri, I. Dobrinovich, F. J. Lahoz, L. A. Oro, Adv. Synth. Catal. 2002, 344, 499-502;
43. f) D. Carmona, M. P. Lamata, L. A. Oro, Eur. J. Inorg. Chem. 2002, 2239-2251;
44. g) J. W. Faller, A. R. Lavoie, Organometallics 2001, 20, 5245-5247;
45. h) H. Y. Rhyoo, Y.-A. Yoon, H.-J. Park, Y. K. Chung, Tetrahedron Lett. 2001, 42, 5045-5048;
46. i) H. Y. Rhyoo, H.-J. Park, Y. K. Chung, Chem. Commun. 2001, 2064-2065;
47. j) H. Y. Rhyoo, H.-J. Park, W. H. Suh, Y. K. Chung, Tetrahedron Lett. 2002, 43, 269-272.
48. For selected reviews on high throughput strategies for catalyst discovery, see: a) K. D. Shimizu, M. L. Snapper, A. H. Hoveyda, Chem. Eur. J. 1998, 4, 1885-1889;
49. b) J. F. Traverse, M. L. Snapper, Drug Discovery Today 2002, 7, 1002-1012.
50. For examples of amino acid-based libraries used in catalysis, see: a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902;
51. b) B. R. Sculimbrene, S. J. Miller, J. Am. Chem. Soc. 2001, 123, 10125-10126;
52. c) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
53. c) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
54. d) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284-4285;
55. e) J. R. Porter, W. G. Wirschun, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657-2658.
56. A. I. Meyers, F. X. Tavares, J. Org. Chem. 1996, 61, 8207-8215.
57. H. Adkins, R. M. Elofson, A. G. Rossow, C. C. Robinson, J. Am. Chem. Soc. 1949, 71, 3622-3629.
58. The reduction of acetophenone with other prominent ligands reported in Table 1 resulted in the following conversion and enantioselectivity after 30 minutes reaction time: V-(S)-4, 65% conv. 97% ee; I-(S)-4, 72% conv. 97% ee.
59. S. Lutsenko, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 2529-2532.
60. D. Swern, K. Omura, Tetrahedron 1978, 34, 1651-1660.
61. A-(rac)-4 is the 1:1 diastereomeric mixture of ligands A-(S)-4 and A-(R)-4. This compound was prepared from L-alanine and racemic 1-amino-2-propanol.
62. K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743; Angew. Chem. Int. Ed. 1998, 37, 1634-1654.
63. K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743; Angew. Chem. Int. Ed. 1998, 37, 1634-1654.
64. 6-arene)(peptide)] complexes, see: a) W. S. Sheldrick, S. Heeb, J. Organomet. Chem. 1989, 377, 357-366;
65. b) R. Krämer, M. Maurus, R. Bergs, K. Polborn, K. Sünkel, B. Wagner, W. Beck, Chem. Ber. 1993, 126, 1969-1980;
66. c) R. Krämer, M. Maurus, K. Polborn, K. Sünkel, C. Robl, W. Beck, Chem. Eur. J. 1996, 2, 1518-1526.
67. a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300; Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
68. a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300; Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
69. b) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466-1478;
70. c) R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7931-7944.
71. For other recent mechanistic discussions, see: a) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580-9588;
72. b) D. G. I. Petra, J. N. H. Reek, J.-W. Handgraaf, E. J. Meijer, P. Dierkes, P. C. J. Kamer, J. Brussee, H. E. Schoemaker, P. W. N. M. van Leeuwen, Chem. Eur. J. 2000, 6, 2818-2829;
73. c) O. Pàmies, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 5052-5058;
74. d) C. P. Casey, J. B. Johnson, J. Org. Chem. 2003, 68, 1998-2001;
75. e) J. B. Johnson, J.-E. Bäckvall, J. Org. Chem. 2003, 68, 7681-7684;
76. f) J.-W. Handgraaf, J. N. H. Reek, E. J. Meijer, Organometallics 2003, 22, 3150-3157.
77. For GLC conditions and retention times, see; ref. [4b].