ortho-metalation of enantiopure aromatic sulfoxides and stereocontrolled addition to imines

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2609-2616

  Le Fur, Nicolas ^a   Mojovic, Ljubica ^a   Plé, Nelly ^a   Turck, Alain ^a   Reboul, Vincent ^b   Metzner, Patrick ^b  

^a Institut de Recherche en Chimie Organique Fine   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC SULFENAMIDES; N-TOSYLIMINES; NUCLEOPHILIC SUBSTITUTION; TERT-BUTYLSULFINYL ARENES;

AMINES; CATALYSIS; CHEMICAL REACTIONS; ISOMERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

IMINE; LITHIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SULFOXIDE; TERT BUTYL TERT BUTANETHIOSULFINATE; THIOSULFINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HEATING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

BENZYLAMINES; CATALYSIS; HYDROCARBONS, AROMATIC; IMINES; LIGANDS; METALS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SULFOXIDES;

EID: 33645548497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052358p     Document Type: Article

References (88)

1. Solladié, G. Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1996; Vol. E21, pp 1056-1076.
2. Mikolajczyk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents (Applications in Asymmetric and Stereoselective Synthesis); CRC Press: Boca Raton, 1997.
3. Allin, S. M.; Shuttleworth, S. J.; Page, P. C. B. Organosulfur Chemistry-Synthetic and Stereochemical Aspects; Page, P. C. B., Ed.; Academic Press: London, 1998; Vol. 2, pp 97-155.
4. Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651-3706.
5. Legros, J.; Dehli, J. R.; Bolm, C. Adv. Synth. Catal. 2005, 347, 19-31.
6. Whisler, M. C.; MacNeil, S. L.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
7. Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1991, 39, 1991-1999.
8. Commerçon, M.; Mangeney, P.; Tejero, T.; Alexakis, A. Tetrahedron: Asymmetry 1990, 1, 287-290.
9. Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17-20.
10. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
11. Beak, P.; Tse, A.; Hawkins, J.; Chen, C.-W.; Mills, S. Tetrahedron 1983, 39, 1983-1989.
12. Matsui, S.; Uejima, A.; Suzuki, Y.; Tanaka, K. J. Chem. Soc., Perkin Trans. 1 1993, 701-705.
13. Matsui, S.; Uejima, A.; Suzuki, Y.; Tanaka, K. Nippon Kagaku Kaishi 1996, 2, 154-159;
14. Chem. Abstr. 1993, 495244.
15. Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 260-265.
16. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726.
17. Pollet, P.; Turck, A.; Plé, N.; Quéguiner, G. J. Org. Chem. 1999, 64, 4512-4515.
18. Snieckus, V.; Beaulieu, F.; Mohri, K.; Han, W.; Murphy, C. K.; Davis, F. A. Tetrahedron Lett. 1994, 35, 3465-3468.
19. Turck, A.; Plé, N.; Pollet, P.; Quéguiner, G. J. Heterocycl. Chem. 1998, 35, 429-436.
20. Le Fur, N.; Mojovic, L.; Plé, N.; Turck, A.; Marsais, F. Tetrahedron 2005, 61, 8924-8931.
21. Masdeu-Bultó, A. M.; Diégueza, M.; Martin, E.; Gómez, M. Coord. Chem. Rev. 2003, 242, 159-201.
22. Bayon, J. C.; Claver, C.; Masdeu-Bultó, A. M. Coord. Chem. Rev. 1999, 193-195, 73-145.
23. Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L. Acc. Chem. Res. 2003, 36, 659-667.
24. Hiroi, K.; Suzuki, Y.; Abe, I.; Hasegawa, Y.; Suzuki, K. Tetrahedron: Asymmetry 1998, 9, 3797-3817.
25. Rebiere, F.; Ricard, O. S. L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991-5999.
26. Baker, R. W.; Hockless, D. C. R.; Pocock, G. R.; Sargent, M. V.; Skelton, B. W.; Sobolev, A. N.; Twiss E.; White, A. H. J. Chem. Soc., Perkin Trans. 1 1995, 2615-2629.
27. Allin, S. M. Organosulfur Chemistry-Synthetic and Stereochemical Aspects; Page, P. C. B., Ed.; Academic Press: London, 1998: Vol. 2, pp 41-61.
28. Khiar, N.; Fernandez, I.; Alcudia, A.; Alcudia, F. Advances in Sulfur Chemistry; Rayner, C., Ed.; JAI Press: Greenwich, CT, 2000: Vol. 2, pp 57-115.
29. Fernandez, I.; Khiar, N.; Liera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789-6796.
30. Fernández, I.; Valdivia, V.; Gori, B.; Alcudia, F.; Álvarez, E.; Khiar, N. Org. Lett. 2005, 7, 1307-1310.
31. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
32. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011-8019.
33. Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317-1320.
34. Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640-2642.
35. Hanquet, G.; Colobert, F.; Lanners, S.; Solladié, G. ARKIVOC 2003, 328-401.
36. Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1989, 30, 7091-7094.
37. Shibutani, T.; Fujihara, H.; Furukawa, N. Tetrahedron Lett. 1991, 32, 2943-2946.
38. Shibutani, T.; Fujihara, H.; Furukawa, N. Tetrahedron Lett. 1991, 32, 2947-2948.
39. Quesnelle, C.; Iihama, T.; Aubert, T.; Perrier, H.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2625-2628.
40. Baker, R. W.; Pocock, G. R.; Sargent, M. V.; Twiss, E. Tetrahedron: Asymmetry 1993, 4, 2423-2426.
41. Nakamura, S.; Yasuda, H.; Watanabe, Y.; Toru, T. J. Org. Chem. 2000, 65, 8640-8650.
42. Risch, N.; Arend, M. Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1996; Vol. E21, pp 1908-1929.
43. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
44. Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
45. Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
46. Durst, T.; LeBelle, M. J.; Van den Eltzen, R.; Tin, K.-C. Can. J. Chem. 1974, 52, 761-766.
47. Astles, P. C.; Mortlock, S. V.; Thomas, E. J. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 1011-1039.
48. Ishii, A.; Komiya, K.; Nakayama, J. J. Am. Chem. Soc. 1996, 118, 12836-12837.
49. Soeta, T.; Nagai, K.; Fujihara, H.; Kuriyama, M.; Tomioka, K. J. Org. Chem. 2003, 68, 9723-9727.
50. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843-3848.
51. Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017.
52. Hiroi, K.; Watanabe, K.; Abe, I.; Koseki, M. Tetrahedron Lett. 2001, 42, 7617-7619.
53. Priego, J.; Mancheño, O. G.; Cabrera, S.; Carretero, J. C. Chem. Commun. 2001, 2026-2027.
54. Priego, J.; Mancheño, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346-1353.
55. Ekegren, J. K.; Roth, P.; Källström, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358-366.
56. Lai, C.-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863-5870.
57. Rowlands, G. J. Synlett 2003, 236-240.
58. Pettinari, C.; Pellei, M.; Cavicchio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 2004, 18, 555-563.
59. Lubbers, T.; Metz, P. Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1996; Vol. E21, pp 2371-2473.
60. Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 834-884.
61. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
62. Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837.
63. Tsuchihashi, G.-i.; Iriuchijima, S.; Maniwa, K. Tetrahedron Lett. 1973, 14, 3389-3392.
64. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6101-6104.
65. Pyne, S. G.; Boche, G. J. Org. Chem. 1989, 54, 2663-2667.
66. Pyne, S. G.; Dikic, B. J. Chem. Soc., Chem. Commun. 1989, 826-827.
67. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998.
68. Bravo, P.; Capelli, S.; Crucianelli, M.; Guidetti, M.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M. Tetrahedron 1999, 55, 3025-3040.
69. Pedersen, B.; Rein, T.; Sotofte, I.; Norrby, P.-O.; Tanner, D. Collect. Czech. Chem. Commun. 2003, 68, 885-898.
70. García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677-680.
71. García-Ruano, J. L.; Alemán, J.; Parra, A. J. Am. Chem. Soc. 2005, 127, 13048-13054.
72. García Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513-516.
73. Charette, A. B.; Giroux, A. Tetrahedron Lett. 1996, 37, 6669-6672.
74. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp 690-700.
75. Eliel, E. L.; Kandasamy, D. J. Org. Chem. 1976, 41, 3899-3904.
76. Nakamura, S.; Yasuda, H.; Toru, T. Tetrahedron: Asymmetry 2003, 13, 1509-1518.
77. Hiroi, K.; Suzuki, Y.; Kaneko, Y.; Kato, F.; Abe, I.; Kawagishi, R. Polyhedron 2000, 19, 525-528.
78. Vries, J. G. d.; Vries, A. H. M. d. Eur. J. Org. Chem. 2003, 799-811.
79. Kang, J.; Kim, D. S.; Kim, J. I. Synlett 1994, 842-844.
80. Arink, A. M.; Braam, T. W.; Keeris, R.; Jastrzebski, J. T. B. H.; Benhaim, C.; Rosset, S.; Alexakis, A.; van Koten, G. Org. Lett. 2004, 6, 1959-1962.
81. Harfouche, J.; Herault, D.; Tommasino, M. L.; Pellet-Rostaing, S.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 3413-3418.
82. Tseng, S.-L.; Yang, T.-K. Tetrahedron: Asymmetry 2005, 16, 773-782.
83. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
84. Braga, A. L.; Alves, E. F.; Silveira, C. C.; Zeni, G.; Appelt, H. R.; Wessjohann, L. A. Synlett 2005, 588-594.
85. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
86. Liu, Z.; Takeuchi, Y. Heterocycles 2002, 56, 693-709.
87. Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727-729.
88. Ahn, K. H.; Kim, S.-K.; Ham, C. Tetrahedron Lett. 1998, 39, 6321-6322.