Ruthenium-catalysed synthesis of fluorinated bicyclic amino esters through tandem carbene addition/cyclopropanation of enynes

Chemistry - A European Journal

Volumn 17, Issue 34, 2011, Pages 9456-9462

  Eckert, Matthieu ^a   Moulin, Solenne ^a   Monnier, Florian ^a   Titanyuk, Igor D ^b   Osipov, Sergey N ^b   Roisnel, Thierry ^a   Dérien, Sylvie ^a   Dixneuf, Pierre H ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

amino acids; bicyclic products; diazoalkanes; enynes; ruthenium

Indexed keywords

ALKENYL GROUPS; AMINO ESTERS; BICYCLIC PRODUCTS; C-H BOND; CARBENES; CARBON-CARBON BOND; CATALYST PRECURSORS; CATALYTIC TRANSFORMATION; CYCLOPROPANATION; DIASTEREO-SELECTIVITY; DIAZO COMPOUNDS; DIAZOALKANES; DOUBLE BONDS; E CONFIGURATION; ENYNES; GOOD YIELD; PROTECTING GROUP; SELECTIVE FORMATION; SINGLE-STEP; TWO-PRODUCT; X-RAY STRUCTURE;

AMINO ACIDS; CARBON DIOXIDE; CARBOXYLATION; CATALYSIS; HEXANE; OLEFINS; RUTHENIUM; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

RUTHENIUM COMPOUNDS;

ALKYNE; AMINE; BICYCLO COMPOUND; CARBENE; DRUG DERIVATIVE; ESTER; FLUORINE; METHANE; ORGANOMETALLIC COMPOUND; PEPTIDOMIMETIC AGENT; PIPECOLIC ACID; PROLINE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DRUG DEVELOPMENT; HALOGENATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMINES; BICYCLO COMPOUNDS; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CYCLIZATION; DRUG DISCOVERY; ESTERS; FLUORINE; HALOGENATION; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PEPTIDOMIMETICS; PROLINE; RUTHENIUM; STEREOISOMERISM;

EID: 80051488259     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101209     Document Type: Article

References (85)

1. Y. Ohfune, T. Shinada, Eur. J. Org. Chem. 2005, 5127-5143
2. G. Licini, L. J. Prins, P. Scrimin, Eur. J. Org. Chem. 2005, 969-977
3. H. Vogt, S. Bräse, Org. Biomol. Chem. 2007, 5, 406-430
4. C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 2007, 18, 569-623.
5. G. R. Marshall, J. D. Clark, J. B. Dunbar, G. D. Smith, J. Zabrocki, A. S. Redlinski, M. T. Leplawy, Int. J. Pept. Protein Res. 1988, 32, 544-555
6. C. Toniolo, E. Benedetti, Macromolecules 1991, 24, 4004-4009.
7. I. Ojima, ChemBioChem 2004, 5, 628-635
8. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-643
9. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886.
10. N. C. Yoder, K. Kumar, Chem. Soc. Rev. 2002, 31, 335-341
11. C. Jäckel, W. Seufert, S. Thust, B. Kolsch, ChemBioChem 2004, 5, 717-720
12. R. Golbik, C. Yu, E. Weyher-Stingl, R. Huber, L. Moroder, N. Budisa, C. Schiene-Fischer, Biochemistry 2005, 44, 16026-16034.
13. V. P. Kukhar, V. A. Soloshonok, in Fluorine-Containing Amino Acids: Synthesis and Properties, Wiley, New York, 1995
14. A. Sutherland, C. L. Willis, Nat. Prod. Rep. 2000, 17, 621-631
15. X.-L. Qiu, W.-D. Meng, F.-L. Qing, Tetrahedron 2004, 60, 6711-6745.
16. A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326
17. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267
18. J. Gante, Angew. Chem. 1994, 106, 1780-1802
19. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720
20. S. Hanessian, L. Auzzas, Acc. Chem. Res. 2008, 41, 1241-1251.
21. A. Nakazato, T. Kumagai, K. Sakagami, R. Yoshikawa, Y. Suzuki, S. Chaki, H. Ito, T. Taguchi, S. Nakanishi, S. Okuyama, J. Med. Chem. 2000, 43, 4893-4909
22. C. Pedregal, W. Prowse, Bioorg. Med. Chem. 2002, 10, 433-436.
23. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834
24. G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236
25. A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436
26. S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382
27. L. Añorbe, G. Dominguez, J. Pérez-Castells, Chem. Eur. J. 2004, 10, 4938-4943
28. C. Bruneau, Angew. Chem. 2005, 117, 2380-2386
29. Angew. Chem. Int. Ed. 2005, 44, 2328-2334
30. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296
31. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
32. V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. 2008, 120, 4338-4386
33. Angew. Chem. Int. Ed. 2008, 47, 4268-4315
34. S. I. Lee, N. Chatani, Chem. Commun. 2009, 371-384.
35. Y. Ni, J. Montgomery, J. Am. Chem. Soc. 2004, 126, 11162-11163
36. C. Nieto-Oberhuber, S. Lopez, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179
37. A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245
38. Y. T. Lee, Y. K. Kang, Y. K. Chung, J. Org. Chem. 2009, 74, 7922-7934.
39. J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569
40. A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786
41. A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869
42. C. Nevado, C. Ferrer, A. M. Echavarren, Org. Lett. 2004, 6, 3191-3194
43. S. Anjum, J. Marco-Contelles, Tetrahedron 2005, 61, 4793-4803
44. D. Brissy, M. Skander, H. Jullien, P. Metailleau, A. Marinetti, Org. Lett. 2009, 11, 2137-2139
45. A. Fürstner, P. Hannen, Chem. Commun. 2004, 2546-2547
46. S. I. Lee, S. M. Kim, M. R. Choi, S. Y. Kim, Y. K. Chung, W.-S. Han, S. O. Kang, J. Org. Chem. 2006, 71, 9366-9372
47. C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet, Chem. Commun. 2009, 6988-6990
48. T. Shibata, Y. Kobayashi, S. Maekawa, N. Toshida, K. Takagi, Tetrahedron 2005, 61, 9018-9024
49. K. Ota, S. I. Lee, J.-M. Tang, M. Takachi, H. Nakai, T. Morimoto, H. Sakurai, K. Kataoka, N. Chatani, J. Am. Chem. Soc. 2009, 131, 15203-15211.
50. V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655
51. Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mourìs, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656-8657
52. M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858-10859
53. F. Gagosz, Org. Lett. 2005, 7, 4129-4132
54. A. Buzas, F. Gagosz, J. Am. Chem. Soc. 2006, 128, 12614-12615
55. N. Marion, P. De Frémont, G. Lemìre, E. D. Stevens, L. Fensterbank, M. Malacria, S. P. Nolan, Chem. Commun. 2006, 2048-2050.
56. N. Chatani, K. Kataoka, S. Murai, J. Am. Chem. Soc. 1998, 120, 9104-9105
57. S. López, E. Herrero-Gomez, P. Pérez-Galan, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 6175-6178
58. Angew. Chem. Int. Ed. 2006, 45, 6029-6032
59. E. J. Cho, M. Kim, D. Lee, Org. Lett. 2006, 8, 5413-5416
60. X. Tong, M. Beller, M. K. Tse, J. Am. Chem. Soc. 2007, 129, 4906-4907
61. L. L. Welbes, T. W. Lyons, K. A. Cychosz, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 5836-5837
62. K. Komeyama, N. Saigo, M. Miyagi, K. Takaki, Angew. Chem. 2009, 121, 10059-10062
63. Angew. Chem. Int. Ed. 2009, 48, 9875-9878.
64. S. Dérien, P. H. Dixneuf, J. Organomet. Chem. 2004, 689, 1382-1392
65. C. Vovard-Le Bray, S. Dérien, P. H. Dixneuf, C. R. Chim. 2010, 13, 292-303.
66. J. Le Paih, S. Dérien, I. ̀zdemir, P. H. Dixneuf, J. Am. Chem. Soc. 2000, 122, 7400-7401
67. J. Le Paih, C. Vovard-Le Bray, S. Dérien, P. H. Dixneuf, J. Am. Chem. Soc. 2010, 132, 7391-7397.
68. F. Monnier, D. Castillo, S. Dérien, L. Toupet, P. H. Dixneuf, Angew. Chem. 2003, 115, 5632-5635
69. Angew. Chem. Int. Ed. 2003, 42, 5474-5477
70. F. Monnier, C. Vovard-Le Bray, D. Castillo, V. Aubert, S. Dérien, P. H. Dixneuf, L. Toupet, A. Ienko, C. Mealli, J. Am. Chem. Soc. 2007, 129, 6037-6049.
71. For a preliminary account of this reaction, see:, M. Eckert, F. Monnier, G. T. Shchetnikov, I. D. Titanyuk, S. N. Osipov, L. Toupet, S. Dérien, P. H. Dixneuf, Org. Lett. 2005, 7, 3741-3743.
72. J. Leroy, C. Wakselman, Can. J. Chem. 1976, 54, 218-225
73. J. R. Del Valle, M. Goodman, Angew. Chem. 2002, 114, 1670-1672
74. Angew. Chem. Int. Ed. 2002, 41, 1600-1602
75. X.-L. Qiu, F.-L. Qing, J. Org. Chem. 2002, 67, 7162-7164
76. X.-L. Qiu, F.-L. Qing, J. Chem. Soc. Perkin Trans. 1 2002, 2052-2057
77. G. Chaume, M.-C. Van Severen, S. Marinkovic, T. Brigaud, Org. Lett. 2006, 8, 6123-6126
78. W. B. Jatoi, A. Bariau, C. Esparcieux, G. Figueredo, Y; Troin, J.-L. Canet, Synlett 2008, 1305-1308
79. C. Caup̀ne, G. Chaume, L. Ricard, T. Brigaud, Org. Lett. 2009, 11, 209-212.
80. S. N. Osipov, A. S. Golubev, N. Sewald, T. Michel, A. F. Kolomiets, A. V. Fokin, K. Burger, J. Org. Chem. 1996, 61, 7521-7528.
81. S. N. Osipov, O. I. Artyushin, A. F. Kolomiets, C. Bruneau, M. Picquet, P. H. Dixneuf, Eur. J. Org. Chem. 2001, 3891-3897.
82. T. Billard, B. R. Langlois, J. Org. Chem. 2002, 67, 997-1000
83. S. Gille, A. Ferry, T. Billard, B. R. Langlois, J. Org. Chem. 2003, 68, 8932-8935.
84. A. Kinoshita, M. Mori, Synlett 1994, 1020-1022.
85. P. J. Fagan, W. S. Mahoney, J. C. Calabrese, I. D. Williams, Organometallics 1990, 9, 1843-1852.