Disulfoxide ligands in rhodium catalyzed asymmetric 1,4-addition: First studies and future directions

Chimia

Volumn 63, Issue 7-8, 2009, Pages 508-511

  Mariz, Ronaldo ^a   Bürgi, Justus ^a   Gatti, Michele ^a   Drinkel, Emma ^a   Luan, Xinjun ^a   Dorta, Reto ^a,b  

^a SCS Mettler Toledo Award Winner   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

1,4 addition; Chiral sulfoxide ligands; Ligand tuning; Rhodium catalysis

Indexed keywords

EID: 70349114279     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2009.508     Document Type: Article

References (69)

1. For recent reviews on sulfide/sulfoxide ligands in catalysis, see:
2. J. C. Bayon, C. Claver, A. M. Masdeu-Bulto, Coord. Chem. Rev. 1999, 193-195, 73;
3. A. M. Masdeu-Bulto, M. Dieguez, E. Martin, M. Gomez, Coord. Chem. Rev. 2003, 242, 159;
4. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133.
5. a) A. L. Walker, Tetrahedron Asymmetry 1992, 3, 961;
6. M. C. Carreno, Chem. Rev. 1995, 95, 1717;
7. H. Pellissier, Tetrahedron 2006, 62, 5559.
8. M. Calligaris, O. Carugo, Coord. Chem. Rev. 1996, 153, 83.
9. For achiral catalysis with sulfoxide ligands, see: a) Y. M. Y. Haddad, H. B. Henbest, J. Husbands, T. R. B. Mitchell, J. Trocha-Grimshaw, J. Chem. Soc., Perkin Trans. I 1974, 596;
10. B. R. James, R. H. J. Morris, Chem. Soc., Chem. Commun. 1978, 929;
11. H. Greenberg, A. Gogoll, J.-E. Bäckvall, J. Org. Chem. 1991, 56, 5808;
12. R. C. Larock, R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584;
13. M. S. Chen, M. C. White, J. Am. Chem. Soc. 2004, 126, 1346;
14. K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois, M. C. White, J. Am. Chem. Soc. 2006, 128, 9032.
15. For attempts showing low selectivities/reactivities: a) B. R. James, R. S. McMillan, Can. J. Chem. 1977, 55, 3927;
16. N. Khiar, I. Fernandez, F. Alcudia, Tetrahedron Lett. 1993, 34, 123;
17. R. Tokunoh, M. Sodeoka, K. Aoe, M. Shibasaki, Tetrahedron Lett. 1995, 36, 8035.
18. For somewhat better selectivities using sulfoxide/nitrogen or sulfoxide/phosphine chelates, see: a) J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymm. 1994, 5, 1895;
19. K. Hiroi, Y. Suzuki, Tetrahedron Lett. 1998, 39, 6499;
20. K. Hiroi, Y. Suzuki, I. Abe, Y Hasegawa, K. Suzuki, Tetrahedron: Asymm. 1998, 9, 3797;
21. D. G. I. Petra, P. C. J. Kamer, A. L. Spek, H. E. Schoemaker, P. W. N. M. van Leeuwen, J. Org. Chem. 2000, 65, 3010;
22. K. Hiroi, Y Suzuki, I. Abe, R. Kawagishi, Tetrahedron 2000, 56, 4701;
23. K. Hiroi, I. Izawa, T. Takizawa, K. Kawai, Tetrahedron 2004, 60, 2155.
24. R. Mariz, X. Luan, M. Gatti, A. Linden, R. Dorta, J. Am. Chem. Soc. 2008, 130, 2172.
25. A. Miashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7933.
26. S) -1 do not react cleanly to give the corresponding complexes. In this case, the tolyl groups on the sulfoxides hinder formation of the dimer, a phenomenon that is also observed for atropisomeric diphosphine ligands incorporating bulky aromatic groups on phosphorous, see: T. Ohshima, H. Tadaoka, K. Hori, N. Sayo, K. Mashima, Chem. Eur. J. 2008, 14, 2060.
27. A. J. Deeming, D. M. Speel, M. Stchedroff, Organometallics 1997, 16, 6004.
28. K. A. Bunten, D. H. Farrar, A. J. Poe, A. Lough, Organometallics 2002, 21, 3344.
29. For comparative studies on the binding ability of sulfoxides to LTMs: a) D. R. Evans, M. Huang, W M. Seganish, J. C. Fettinger, T. L. Williams, Inorg. Chem. Commun. 2003, 6, 462.
30. R. Dorta, H. Rozenberg, L. J. W. Shimon, D. Milstein, Chem. Eur. J. 2003, 9, 5237.
31. Y Takaya, M. Ogasawara, T. Hayashi, M. Sakai, M. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579.
32. For a review, see: a) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829. With BINAP and its derivatives, see:
33. S. Sakuma, M. Sakai, R. Itooka, N. Miyaura, J. Org. Chem. 2000, 65, 5951;
34. J.-P. Genet, Synlett 2002, 11, 1791;
35. M. Pucheault, S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2002, 3552;
36. R. Itooka, Y Iguchi, N. Miyaura, J. Org. Chem. 2003, 68, 6000. With phosphoramidites and phosphonites, see:
37. M. T. Reetz, D. Moulin, A. Gosberg, Org. Lett. 2001, 3, 4083;
38. J.-G. Boiteau, R. Imbos, A. J. Minaard, B. L. Feringa, Org. Lett. 2003, 5, 681;
39. J.-G. Boiteau, A. J. Minaard, B. L. Feringa, J. Org. Chem. 2003, 68, 9481;
40. S. L. X. Martina, A. J. Minaard, B. Hessen, B. L. Feringa, Tetrahedron Lett. 2005, 46, 7159;
41. K. Kurihara, N. Sugushita, K. Oshita, D. Piao, Y. Yamamoto, N. Miyaura, J. Organomet. Chem. 2007, 692, 428. With chiral dienes:
42. T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508;
43. C. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873;
44. J.-F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850;
45. Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503;
46. J.-F. Paquin, C. R. J. Stephenson, C. Defieber, E. M. Carreira, Org. Lett. 2005, 7, 3821;
47. A. Kina, K. Ueyama, T. Hayashi, Org. Lett. 2005, 7, 5889;
48. F.-X. Chen, A. Kina, T. Hayashi, Org. Lett. 2006, 8, 341;
49. T. Nishimura, M. Nagaosa, T. Hayashi, Chem. Lett. 2008, 37, 860;
50. T. Gendrineau, O. Chuzel, H. Eijsberg, J.-P. Genet, S. Darses, Angew. Chem. Int. Ed. 2008, 47, 7669. With chiral P-olefin ligands:
51. R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. Int. Ed. 2005, 44, 4611;
52. E. Piras, F. Läang, H. Rüegger, D. Stein, M. Wörle, H. Grützmacher, Chem. Eur. J. 2006, 12, 5849;
53. P. Kasak, V. B. Arion, M. Widhalm, Tetrahedron: Asymmetry 2006, 17, 3084;
54. W.-L. Duan, H. Iwamura, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 2130;
55. R. Mariz, A. Briceno, R. Dorta, R. Dorta, Organometallics 2008, 27, 6605.
56. a) 'Comprehensive Organometallic Chemistry', Eds. E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon Press, Oxford, Vol. 12, 1995;
57. R. H. Crabtree, 'The Organometallic Chemistry of the Transition metals', Wiley, New York, 1994;
58. W. R. Moser, D. W. Slocum, 'Homogeneous Transition metal Catalyzed Reactions', Eds. Adv. Chem. Ser. 230, 1992;
59. 'Applied Homogeneous Catalysis with Organometallic Compounds', Eds. B. Cornils, W A. Herrmann, VCH, Weinheim, 1996.
60. For interesting investigations on the relationship between bite angle and electronic structure see: a) P. Hofmann, C. Meier, U. Englert, M. U. Schmidt, Chem. Ber. 1992, 125, 353;
61. Z. Freixa, P. W. N. M. van Leeuwen, Dalton Trans. 2003, 1890.
62. a) R. Schmid, M. Cereghetti, B. M. Heiser, P. Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897;
63. X. Zhang, K. Mashima, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa, H. Takaya, Tetrahedron Lett. 1991, 32, 7283.
64. I. Fernández, N. Khiar, J. M. Llera, F. Alcudia, J. Org. Chem. 1992, 57, 6789.
65. a) C. A. Tolman, Chem. Rev. 1977, 77, 312;
66. T. L. Brown, Inorg. Chem. 1995, 34, 2718;
67. R. S. Drago, S. Joerg, J. Am. Chem. Soc. 1996, 118, 2654;
68. A. Fernandez, C. Reyes, M. R. Wilson, D. C. Woska, A. Prock, W. P. Giering, Organometallics 1997, 16, 342;
69. S. Joerg, R. S. Drago, J. Sales, Organometallics 1998, 17, 589.