Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: Chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis

Chemistry - A European Journal

Volumn 12, Issue 3, 2006, Pages 667-675

  Albano, Vincenzo Giulio ^a   Bandini, Marco ^a   Barbarella, Giovanna ^b   Melucci, Manuela ^b   Monari, Magda ^a   Piccinelli, Fabio ^a   Tommasi, Simona ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b CNR   (Italy)

Author keywords

Asymmetric catalysis; Electronic interactions; Palladium; Thiophenes; X ray diffraction

Indexed keywords

ASYMMETRIC CATALYSIS; ELECTRONIC INTERACTIONS; ORGANOMETALLIC CATALYSTS; THIOPHENES;

AMINES; COMPLEXATION; MOLECULAR DYNAMICS; PALLADIUM; STEREOCHEMISTRY; SULFUR COMPOUNDS;

CATALYSTS;

DIAMINE; LIGAND; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; DIAMINES; LIGANDS; STEREOISOMERISM; THIOPHENES;

EID: 30744467168     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500889     Document Type: Article

References (53)

1. I. Ojima, in Catalytic Asymmetric Synthesis, Vol. II, Wiley-VCH, New York, 2000.
2. Comprehensive Asymmetric Catalysis (Eds.: N. E. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
3. R. Fiammengo, C. M. Bruinink, M. Crego-Calama, D. N. Reinhoudt, J. Org. Chem. 2002, 67, 8552-8557.
4. a) M. McGarrigle, D. M. Murphy, D. G. Gilheany, Tetrahedron: Asymmetry 2004, 15, 1343-1354;
5. b) P. B. Armstrong, L. M. Bennett, R. N. Constantine, J. L. Fields, J. P. Jasinski, R. J. Staples, R. C. Bunt, Tetrahedron Lett. 2005, 46, 1441-1445.
6. For a recent example of chiral organometallic catalysis inspired to bio-catalyzed transformations, see: D. Magdziak, G. Lalic, H. M. Lee, K. C. Fortner, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2005, 127, 7284-7285.
7. For a recent example of chiral organic catalysis inspired to bio-catalyzed transformations, see: S. G. Quellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 32-33.
8. a) M. O. Wolf, Adv. Mater. 2001, 13, 545-553;
9. b) B. J. Holliday, T. M. Swager, Chem. Commun. 2005, 23-56.
10. E. Holder, B. M. W. Langeveld, U. S. Schubert, Adv. Mater. 2005, 17, 1109-1121.
11. a) D. Fichou, in Handbook of Oligo- and Polythiophenes, Wiley-VCH, Weinheim, 1999;
12. b) T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds, in Handbook of Conducting Polymers, Marcel Dekker, New York, 1998.
13. a) S. Lamansky, P. Djurovich, D. Murphy, F. Adbel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Mui, R. Bau, M. E. Thompson, Inorg. Chem. 2001, 40, 1704-1711;
14. b) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304-4312;
15. c) C. Moorlag, M. O. Wolf, C. Bohne, B. O. Patrick, J. Am. Chem. Soc. 2005, 127, 6382-6393.
16. a) L. Latos-Grazynski, J. Lisowski, P. Chmielewski, M. Grzeszczuk, M. M. Olmstead, A. L. Balch, Inorg. Chem. 1994, 33, 192-197;
17. b) O. C. Clot, M. O. Wolf, B. O. Patrick, J. Am. Chem. Soc. 2001, 123, 9963-9973;
18. c) X. Fang, J. G. Watkin, B. L. Scott, G. J. Kubas, Organometallics 2001, 20, 3351-3354;
19. d) B.-F. Bonini, L. Giordano, M. Fochi, M. Comes-Franchini, L. Bernardi, E. Capitò, A. Ricci, Tetrahedron: Asymmetry 2004, 15, 1043-1051.
20. Palladium Reagents and Catalysis. New Perspectives for the 21st Century (Ed.: J. Tsuji), Wiley, New York, 2004.
21. V. G. Albano, M. Bandini, M. Melucci, M. Monari, F. Piccinelli, S. Tommasi, A. Umani-Ronchi, Adv. Synth. Cat. 2005, 347, 1507-1512.
22. S.-H. Kim, E.-K. Lee, G.-J. Kim, Bull. Korean Chem. Soc. 2004, 25, 754-756.
23. B. M. Trost, D. L. Van Vraken, Chem. Rev. 1996, 96, 395-422.
24. Phenomena of hemilability are frequently invoked in the rationalization of numerous organometallic catalyses. For a recent review regarding P/P(O) ligands, see: V. V. Grushin, Chem. Rev. 2003, 103, 1629-1662.
25. 0-HO interactions were recently reported on stabilizing Pd-BOX catalysts for AAA: K. Hallman, A. Frolander, T. Wondimagegn, M. Svensson, C. Moberg, Proc. Natl. Acad. Sci. USA 2004, 101, 5400-5404.
26. J. Roncali, Chem. Rev. 1997, 97, 173-205.
27. J. Casado, T. M. Pappenfus, L. L. Miller, K. R. Mann, E. Ortí, P. M. Viruela, R. Pou-Amérigo, V. Hernández, J. T. L. Navarrete, J. Am. Chem. Soc. 2003, 125, 2524-2534.
28. H. Higuchi, Y. Uraki, H. Yokota, H. Koyama, J. Ojima, T. Wanda, H. Sasabe, Bull. Chem. Soc. Jpn. 1998, 71, 483-495.
29. H.-P. Hu, H.-L. Chen, Z. Zheng, Adv. Synth. Catal. 2005, 347, 541-548.
30. Unfortunately, the use of the pyrrolidine-based ligand 3f in the AAA with 4c was ruled out by formation, during the course of the reaction, of a dark brown, highly insoluble solid that removed the chiral Pd catalyst from the solution. Although a detailed investigation has not been performed so far, this peculiar behavior of 3f could be ascribed to a side interaction of the silver salt with the pyrrolidine units present in oligothienyl side arms.
31. L. B. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J. R. Reynolds, Adv. Mater. 2000, 12, 481-494.
32. J.-M. Raimundo, P. Blanchard, P. Frère, N. Mercier, I. Ledoux-Rak, R. Hierle J. Roncali, Tetrahedron Lett. 2001, 42, 1507-1510.
33. a) T. Yamagishi, M. Ohnuki, T. Kiyooka, D. Masai, K. Sato, M. Yamaguchi, Tetrahedron: Asymmetry 2003, 14, 3275-3279;
34. b) B. M. Trost, A. C. Krueger, R. C. Bunt, J. Zambrano, J. Am. Chem. Soc. 1996, 118, 6520-6521;
35. c) T. P. Clark, C. R. Landis, J. Am. Chem. Soc. 2003, 125, 11792-11793;
36. d) O. Pàmies, M. Diéguez, C. Claver, J. Am. Chem. Soc. 2005, 127, 3646-3647.
37. J. M. Canal, M. Gómez, F. Jiménez, M. Rocamore, G. Muller, E. Duñach, D. Franco, A. Jiménez, F. H. Cano, Organometallics 2000, 19, 966-978.
38. a) P. R. Auburn, P. B. Mackenzie, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2033-2046;
39. b) P. B. Mackenzie, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2046-2054.
40. a) P. Dierkes, S. Ramdeehul, L. Barloy, A. De Cian, P. C. J. Fisher, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299-3301;
41. Angew. Chem. Int. Ed. 1998, 37, 3116-3118;
42. b) S. Ram deehul, P. Dierkes, R. Aguado, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3302-3304;
43. Angew. Chem. Int. Ed. 1998, 37, 3118-3121.
44. H. Steinhagen, M. Reggelin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202;
45. Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110.
46. L. Canovese, G. Chessa, F. Visentin, P. Uguagliati, Coord. Chem. Rev. 2004, 248, 945-954.
47. S. Bahmanyar, B. C. Borer, Y. M. Kim, D. M. Kurtz, S. Yu, Org. Lett. 2005, 7, 1011-1014.
48. M. D'Auria, A. De Mico, F. D'Onofrio, G., Piancastelli, J. Org. Chem. 1987, 52, 5243-5247.
49. Y. Zhang, A.-B. Hoernfeld, S. Gronowitz, J. Heterocycl. Chem. 1995, 32, 771-777.
50. F. Effenberg, F. Würthner, F. Steybe, J. Org. Chem. 1990, 55, 2082-2091.
51. M. M. M. Raposo, G. Kirsch, Tetrahedron 2003, 59, 4891-4899.
52. P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615;
53. Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568.