Asymmetric amino acid catalysis

AIP Conference Proceedings

Volumn 979, Issue , 2008, Pages 47-59

  Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Amino acids; Asymmetric amplification; Asymmetric catalysis; Non linear effects; Sugars

Indexed keywords

EID: 40849124266     PISSN: 0094243X     EISSN: 15517616     Source Type: Conference Proceeding    
DOI: 10.1063/1.2901846     Document Type: Conference Paper

References (88)

1. (a) W. A. Bonner, Orig. Life Evol. Biosphere 21, 59. (1991).
2. (b) J. L. Bada, Nature 374, 594. (1995).
3. (c) S. F. Mason, Nature 314, 400. (1985).
4. J. R. Cronin, S. Pizzarello, Science 275, 951. (1997).
5. G. Cooper, N. Kimmich, W. Belisle, J. Sarinana, K. Brabham, L. Garrel, Nature 414, 879. (2001).
6. (a) J. Baily, A. Chrysostotomou, J. H. Hough, T. M. Gledhill, A. McCall, S. Clark, F. Ménard, M. Tamura, Science 281, 672. (1998).
7. (b) B. Norden, Nature 266, 567. (1977).
8. F. C. Frank, Biochem. Biophys. Acta 11, 459. (1953).
9. K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 378, 767. (1995).;
10. T. Shibata, H. Morioka, T. Hayase, K. Choji, K. Soai, J. Am. Chem. Soc. 118, 471. (1996).;
11. T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai, K. Soai, J. Am. Chem. Soc. 120, 12157. (1998).;
12. K. Soai, I. Sato, Enantiomer 6, 189. (2001).
13. (a) A. Córdova, H. Sundén, M. Engqvist, I. Ibrahem, J. Casas, J. Am. Chem. Soc. 126, 8914. (2004).;
14. (b) S. Pizzarello, A. L. Weber, Science 303, 1151. (2004).
15. (c) A. Córdova, I. Ibrahem, J. Casas, H. Sundén, M. Engqvist, E. Reyes, Chem. Eur. J. 11, 4772. (2005).
16. For original work on non-linear effect in proline-catalyzed reactions see: (a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 108, 2353. (1986), see also:
17. (b) L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 125, 16. (2003).
18. a) S. Hanessian, V. Pham, Org. Lett. 2, 2975. (2000).
19. (b) S. P. Mathew, H. Iwamura, D. Blackmond, Angew. Chem. Int. Ed. 43, 3317. (2004).
20. (c) H. Iwamura, S. P. Mathew, D. Blackmond, J. Am. Chem. Soc. (126), 11770. (2004).
21. (d) A. Córdova, M. Engqvist, I. Ibrahem, J. Casas, H. Sundén, Chem. Commun. 2047. (2005).
22. (e) A. Córdova, H. Sundén, Y. Xu, I. Ibrahem, W. Zou, M. Engqvist, Chem. Eur. J. 12, 5446. (2006).
23. (a) Y. Hayashi, M. Matsuzuwa, J. Yamaguchi, S. Yonehara, Y. Matsumoto, M. Shoji, D. Hashizume, H. Koshino, Angew. Chem. Int. Ed. 45, 4593. 2006.
24. (b) M. Klussmann, H. Iwamura, S. P. Mathew, D. H. Wells, Jr., U. Pandya, A. Armstrong, D. G. Blackmond, Nature 441, 621. (2006).
25. (c) M. Klussmann, A. J. P. White, A. Armstrong, D. G. Blackmond, Angew. Chem. Int. Ed. 45, 7985. (2006).
26. (d) Armando Córdova, Weibiao Zou, Pawel Dziedzic, Ismail Ibrahem, Efraim Reyes, Yongmei Xu, Chem. Eur. J. 12, 5383. (2006).
27. (e) A. Córdova, W. Zou, P. Dziedzic, I. Ibrahem, E. Reyes, Y. Xu, Chem. Eur. J. 12, 5175. (2006).
28. (f) R. Breslow, M. S. Levine, Proc. Nat. Acad. Sci. U. S. A. 103, 12979. (2004).
29. (g) P. Dziedzic, I. Ibrahem, H. Sundén, A. Córdova, Tetrahedron Lett. 47, 6657. (2006).
30. (h) P. Dziedzic, I. Ibrahem, H. Sundén, A. Córdova, Tetrahedron Lett. 48, 1875. (2007). For asymmetric amplification of amino acids by sublimation see:
31. (i) S. P. Fletcher, R. B. C. Jagt, B. L. Ferringa, Chem. Commun. 2578. (2007).
32. (a) Z. G. Hajos, D. R. Parrish, German Patent DE 2102623 (July 29, 1971).
33. (b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 39, 1615. (1974).
34. U. Eder, G. Sauer, R. Wiechert, German Patent DE 2014757 (Oct. 7, 1971).
35. (b) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. 10, 496. (1971).
36. a) S. Danishefsky, P. Cain, J. Am. Chem. Soc. 97, 5282. (1975).
37. (b) I. Shimizu, Y. Naito, J. Tsuji, Tetrahedron Lett. 21, 4975. (1980).
38. (c) H. Hagiwara, H. Uda, J. Org. Chem. 53, 2308. (1988).
39. (d) E. J. Corey, S. C. Virgil, J. Am. Chem. Soc. 112, 6429. (1990).
40. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 122, 2395. (2000).
41. W. Notz, B. List, J. Am. Chem. Soc. 122, 7386. (2000).
42. For selected early contributions on the proline-catalyzed intermolecular aldol reaction see: (a) P. I. Dalko, L. Moisan, Angew Chem. Int. Ed. 40, 3726. (2001).
43. (b) B. List, Tetrahedron 58, 5573. (2002).
44. (c) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 43, 5138. (2004).
45. See also some selected early papers: (d) B. List, P. Pojarliev, C. Castello, Org. Lett. 3, 573. (2001).
46. (e) K. S. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 123, 5260. (2001).
47. (f) A. Córdova, W. Notz, C. F. Barbas III, Chem. Commun. 67, 3034. (2002).
48. (g) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 67, 301. (2002).
49. (h) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 124, 6798. (2002).
50. (i) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620.
51. (j) B. List, L. Hoang, H. J. Martin, Proc. Natl. Acad. Sci. U.S.A. 101, 5839. (2004).
52. (k) A. I. Nyberg, A. Usano, P. Pihko, Synlett 1891. (2004).
53. D. Seebach, A. K. Beck, D. M. Badine, M. Limbach, A. Eschenmoser, A. M. Treasurywala, R. Hobi, W. Prikoszovich, B. Linder, Helvetica Chemica Acta 90, 425. (2007).
54. H. Sundén, M. Engqvist, J. Casas, I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed. 43, 6532. (2004).
55. A. Córdova, W. Zou, I. Ibrahem, E. Reyes, M. Engqvist, W.-W. Liao, Chem. Commun. 3586. (2005).
56. For DFT calculations on the acyclic amino acid-catalyzed intermolecular aldol reaction see (a) A. Bassan, W. Zou, E. Reyes, F. Himo, A. Córdova, Angew. Chem. Int. Ed. 44, 7028. (2005).
57. (b) For DFT calculations of the acyclic amino acid-catalyzed intramolecular aldol reaction see: F. R. Clemente, K. N. Houk, J. Am. Chem. Soc. 127, 11294. (2005).
58. For selected examples of highly enantioselective intermolecular aldol reactions catalyzed by amino acids with a primary amine functionality see: reference 10d. (a) Z. Jiang, Z. Liang, X. Wu, Y. Lu, Chem. Commun. 2801. (2006).
59. (b) D.-S. Deng, J. Cai, Helv. Chim. Acta 90, 119. (2007).
60. (c) X. Wu, Z. Jian, H. -M. Shen, Y. Lu, Adv. Synth. Catal. 349, 812. (2007).
61. (d) S. S. V. Ramasastry, H. Zhang, F. Tanaka, C. F. Barbas III. J. Am. Chem. Soc. 129, 288. (2007).
62. (e) S. S. V. Ramasastry, K. Albertshofer, N. Utsumi, F. Tanaka, C. F. Barbas III Angew. Chem. Inter. Ed. 46, 5572. (2007).
63. See also: (f) M. Amedjkouh, Tetrahedron: Asymmetry 16, 1411. (2005).
64. (g) M. Limbach, Tetrahedron Lett. 47, 3843. (2006).
65. (h) I. Ibrahem, W. Zou, M. Engqvist, Y. Xu, A. Córdova, Chem. Eur. J. 11, 7025. (2005).
66. (i) Y. Xu, A. Córdova, Chem. Commun. 460. (2006).
67. (j) Y. Xu, W. Zou, H. Sundén, I. Ibrahem, A. Córdova, Adv. Synth. Cat. 348, 418. (2006).
68. (a) W.-D. Fessner, In Stereoselective Biocatalysis, edited by R. N. Patel, New York, Marcel Dekker, 2000, 239.
69. (b) Machajewski, T. D.; Wong, C. -H. Angew. Chem. Int. Ed. 39, 1352. (2000).
70. (c) A. Heine, G. DeSantis, J. G. Luz, M. Mitchell, C. -H. Wong, I. A. Wilson, Science 294, 369. (2001).
71. (a) W. Zou, I. Ibrahem, P. Dziedzic, H. Sundén, A. Córdova, Chem. Commun. 4946. (2005).
72. (b) P. Dziedzic, W. Zou, J. Hafren, A. Córdova, Org. Biol. Chem. 4, 38. (2006). See also:
73. (c) A. L. Weber, S. Pizzarrello, Proc. Nat. Acad. Sci. U. S. A. 103, 12713. (2006).
74. (d) G. Carrea, G. Ottolina, A. Lazcano, V. Pironti, S. Colonna, Tetrahedron: Asymmetry 18, 1265. (2007).
75. A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan Angew. Chem. Int. Ed. 43, 2152. (2004).
76. (a) E. Reyes, A. Córdova, Tetrahedron Lett. 46, 6605. (2005). Proline can also react with glucose according to the Maillard reaction see:
77. (b) I. Blank, S. Devaud, W. Matthey-Doret, F. Robert, J. Agric. Food Chem. 51, 3643. (2003).
78. (a) A. Bøgevig, H. Sundén, A. Córdova, Angew. Chem. Int. Ed. 43, 1109. (2004).
79. (b) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Angew. Chem. Int Ed. 43, 1112. (2004).
80. (c) P. Merino, T. Tejero, Angew. Chem. Int. Ed. 43, 2995. (2004).
81. (d) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 10, 3673. (2004).
82. (e) P. H.-Y. Cheong, K. N. Houk, J. Am. Chem. Soc. 126, 13912. (2004).
83. E. M. Vogel, H. Gröger, M. Shibasaki, Angew. Chem. Int. Ed. 38, 1570. (1999). See also:
84. J. E. Imbriglio, M. M. Vasbinder, S. J. Miller, Org. Lett. 5, 3741. (2003).
85. H. Iwamura, D. H. Wells, J. S. P. Mathew, M. Klussmann, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 126, 16312. (2004).;
86. A. Hartikka, P. I. Arvidsson, Eur. J. Org. Chem. 4287. (2005).
87. I. Ibrahem, H. Sundén, P. Dziedzic, R. Rios, A. Córdova, Adv. Synth. Cat. 349, 1868. (2007).
88. H. Sundén, R. Rios, I. Ibrahem, Jan Vesely, P. Dziedzic, A. Córdova, Experimental results to be published.