The First Catalytic Highly Enantioselective Alkylation of Ketimines - A Novel Approach to Optically Active Quaternary α-Amino Acids

Chemistry - A European Journal

Volumn 9, Issue 24, 2003, Pages 6145-6154

  Saaby, Steen ^a   Nakama, Kimitaka ^a   Lie, Mette Alstrup ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

amino acids; Alkylation; Asymmetric catalysis; Zinc

Indexed keywords

ALKYLATION; CATALYSIS; COMPLEXATION; MOLECULAR STRUCTURE; NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ENANTIOSELECTIVITY;

AMINO ACIDS;

ALPHA AMINO ACID; IMINE; KETIMINE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; ENANTIOSELECTIVITY; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETALS; ALKYLATION; AMINO ACIDS; CATALYSIS; ETHYLENES; IMINES; KETONES; LIGANDS; METALS; MODELS, CHEMICAL; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 0346732156     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305302     Document Type: Article

References (83)

1. For recent reviews on asymmetric synthesis of quaternary carbon centers see: a) M. Cristoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
2. For recent reviews on asymmetric synthesis of quaternary carbon centers see: a) M. Cristoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
3. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401.
4. b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401.
5. For review see for example: C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3517-3599.
6. a) G. Fenteany, R. F. Standaert, W. S. Lane, S. Choi, E. J. Corey, S. L. Schreiber, Science 1995, 268, 726-731;
7. b) G. Jung, H. Brüchner, H. Schmidt in Structure and Activity of Natural Peptides, (Eds.: W. Voelter, G. Wietzel), de Gruyter, Berlin, 1981;
8. c) D. Kluepfel, J. F. Bagli, H. Baker, M. P. Charest, A. Kudelski, S. N. Sehgal, C. J. Vézina, J. Antibiot. 1972, 25, 109-115;
9. d) M. Oka, N. Kato. J. Enzyme Inhib. 2001, 16, 465-473.
10. a) P. K. C. Paul, M. Sukumar, R. Bardi, A. M. Piazzesi, G. Valle, C. Toniolo, P. Balaram, J. Am. Chem. Soc. 1986, 108, 6363-6370;
11. b) M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086, and references therein.
12. See for example: a) R. Sarges, J. Bordner, B. W. Donimy, M. J. Peterson, E. B. Whipple, J. Med. Chem. 1985, 28, 1716-1720;
13. b) T. Yamaguchi, K. Miura, T. Usui, R. Unno, Y. Matsumoto, M. Fukushima, K. Mizuno, Y. Kondo, Y. Baba, M. Kurono, Arzneim.-Forsch. 1994, 44, 344-348;
14. c) H. U. Stilz, B. Jablonka, M. Just, J. Knolle, E. F. Paulus, G. Zoller, J. Med. Chem. 1996, 39, 2118-2122;
15. d) N. Hotta, T. Touota, K. Matsuoka, Y. Shigeta, R. Kikkiwa, T. Kaneko, A. Takahashi, K. Sugimura, Y. Koike, J. Ishii, N. Sakamoto, Diabetes Care 2001, 24, 1776-1782.
16. J. C. Ruble, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 11532-11533.
17. a) Y. Ito, R. Kuwano, J. Am. Chem. Soc. 1999, 121, 3236-3237;
18. b) B. M. Trost, X. Ariza, Angew. Chem. 1997, 109, 2749-2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637;
19. b) B. M. Trost, X. Ariza, Angew. Chem. 1997, 109, 2749-2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637;
20. c) B. M. Trost, X. Ariza, J. Am. Chem. Soc. 1999, 121, 10727-10737;
21. d) B. M. Trost, K. Dogra, J. Am. Chem. Soc. 2002, 124, 7256-7257.
22. a) E. N. Jacobsen, P. Vachal, Org. Lett. 2000, 2, 867-870;
23. b) E. N. Jacobsen, P. Vachal, J. Am. Chem. Soc. 2002, 124, 10012-10014;
24. c) K. Funabashi, H. Ratni, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 10784-10785;
25. d) J. J. Burne, M. Chavarot, P. Y. Chavant, Y. Vallée, Tetrahedron Lett. 2000, 41, 873-876;
26. e) M. Chavarot, J. J. Burne, P. Y. Chavant, Y. Vallée, Tetrahedron: Asymmetry 2001, 12, 1147-1150.
27. Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron 1988, 44, 5253-5262.
28. For Lewis acid catalyzed enantioselective addition reactions of imines derived from α-dicarbonyl compounds, see for example: a) A. E. Taggi, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10-19;
29. b) A. Fujii, E. Hagawara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458; Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641;
30. b) A. Fujii, E. Hagawara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458; Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641;
31. d) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339;
32. e) H. Kagoshima, T. Uzawa, T. Akiyama, Chem. Lett. 2002, 298-299;
33. f) Chem. Eur. J. 2000, 6, 2435-2448;
34. g) S. Saaby, P. Bayón, S. P. Aburel, K. A. Jørgensen, J. Org. Chem. 2002, 67, 4352-4361, and references therein.
35. For review, see: a) E. F. Kleinmann, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Flemming), Pergamon Press, Oxford, 1991, Vol 2, Chapter 4.1, p. 893;
36. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122; Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
37. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122; Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
38. For Lewis acid catalyzed enantioselective Mannich reactions of aldimines, see: a) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
39. b) M. Ueno, H. Ishitani, S. Kobayashi, Org. Lett. 2002, 4, 3395-3397;
40. c) S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334; Angew. Chem. Int. Ed. 2001, 40, 2271-2274;
41. c) S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334; Angew. Chem. Int. Ed. 2001, 40, 2271-2274;
42. d) S. Kobayashi, R. Matsubara, H. Kitagawa, Org. Lett. 2002, 4, 143-145;
43. e) S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507-2515;
44. f) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron Lett. 1999, 40, 307-310;
45. g) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 8857-8867;
46. h) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712-4713;
47. i) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085; Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
48. i) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085; Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
49. j) L. Bernardi, A. S. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583-2591;
50. for Lewis base catalyzed enantioselective Mannich reactions of aldimines, see k) K. Tomioka, H. Fujieda, S. Hayashi, M. A. Hussein, T. Kambara, Y. Nomura, M. Kanai, K. Koga, Chem. Commun. 1999, 715-716;
51. l) H. Fujieda, M. Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061;
52. organocatalyzed enantioselective Mannich reactions of aldimines, see: m) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964-12965;
53. n) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
54. o) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
55. p) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
56. q) A. Córdova, S. Watanaba, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867;
57. r) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
58. (R,R)-Ph-pybox: 2,6-Bis[4′-(R)-phenyloxazolin-2′ -yl]-pyridine. For review, see: G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev. 2003, 103, 3119-3154.
59. For leading references to the application of pybox ligands in asymmetric catalysis see: a) H. Nishiama, M. Kondo, T. Nakamura, K. Itoh, Organometallics 1991, 10, 500-508.
60. b) D. A. Evans, D. M. Barnes, J. F. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594.
61. 2 complexed with chiral ligands of the phosphino-oxazoline-, bisoxazoline- or BINAP-types catalyzed the reaction of imine la and silylketene acetal 6a in high yields, but in general with low enantioinduction.
62. S. Kobayashi, Y. Fujishita, T. Mukaiyama, Chem. Lett. 1990, 1455-1458.
63. 2, the Mannich reaction of 1a with 6a proceeds in quantitative yield in less than 2 h at -78 °C.
64. CCDC-207535 contains the supplementary crystallographic data for compound 10. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB21EZ, UK; fax: (+44)1223-336-033; or e-mail: deposit@ccdc. cam.ac.uk).
65. For review, see: a) C. Girard, H. G. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2923-2959;
66. For review, see: a) C. Girard, H. G. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2923-2959;
67. b) H. B. Kagan, T. O. Luukas, in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2000, Chapter 4.1, pp. 1-16.
68. 2 for 1 h and then cooled to - 78 °C.
69. CCDC-214298 contains the supplementary crystallographic data for compound 11. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB21EZ, UK; fax: (+44)1223-336-033; or e-mail: deposit@ccdc. cam.ac.uk).
70. a) H. C. Aspinall, N. Greeves, J. Organomet. Chem. 2002, 647, 151-157;
71. b) C. Provent, G. Bernardinelli, A. F. Williams, N. Vulliermet Eur. J. Inorg. Chem. 2001, 1963-1967;
72. c) M. Jiang, S. Dalgarno, C. A. Kilner, M. A. Halcrow, T. P. Kee, Polyhedron 2001, 20, 2151-2162.
73. MS-analysis showed the existence of a 7a-Zn-OH complex in the crude product mixture.
74. Density functional theory (DFT) calculations were performed by using the Gaussian 98 software. The B3LYP method and the 6-31G(D,P) basis set were chosen. (Gaussian 98, Revision A.7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian Inc., Pittsburgh PA, 1998).
75. Loss of optical purity was not detected throughout the transformation shown in Scheme 4.
76. Example of a catalytic asymmetric allylation of a novel ketimine electrophile with intrinsic protecting group anchoring.
77. J. P. Versleijen, M. S. Sanders-Hovens, S. A. Vanhommerig, J. A. Vekemans, E. M. Meijer, Tetrahedron 1993, 49, 7793-7802.
78. E. Juaristi, J. S. Cruz-Sánches, J. Org. Chem. 1988, 53, 3334-3338.
79. Y. Kita, J. Segawa, J. Haruta, H. Yasuda, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 1988, 1099-1104.
80. N. Slougui, G. Rousseau, Synth. Commun. 1987, 17, 1-11.
81. a) G. M. Rubottom, J. M. Gruber, R. Marrero, H. D. Juve, Jr., C. W. Kim, J. Org. Chem. 1983, 48, 4940-4944;
82. b) T. V. Rajababu, J. Org. Chem. 1984, 49, 2083-2089.
83. J. G. Grunwell, A. Karipides, C. T. Wigal, S. W. A. Clayton, F. J. Fleitz, M. Daffner, J. E. Stevens, J. Org. Chem. 1991, 56, 91-95.