Asymmetrie ruthenium-catalyzed 1,4-additions of aryl thiols to enones

Organic and Biomolecular Chemistry

Volumn 8, Issue 1, 2010, Pages 193-200

  Bǎdoiu, Andrei ^a   Bernardinelli, Gerald ^a   Besnard, Céline ^a   Peter Kundig E ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CYCLOADDITION REACTION; LEWIS ACID; PRODUCT SELECTIVITIES; REACTION MECHANISM; RU COMPLEXES; RUTHENIUM COMPLEXES; S-TRANS; UNSATURATED CARBONYL COMPOUNDS; X-RAY STRUCTURE;

ADDITION REACTIONS; CARBONYLATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM; UNSATURATED COMPOUNDS;

RUTHENIUM COMPOUNDS;

ALKENE; KETONE; RUTHENIUM DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; BINDING SITE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKENES; BINDING SITES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; KETONES; RUTHENIUM COMPOUNDS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 76849097399     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b918877k     Document Type: Article

References (82)

1. (a) F. da Silva, Jr, R. J. Williams, The Biological Chemistry of the Elements, Oxford University Press, New York, 2001;
2. (b) C. Chatgilialoglu, K.-D. Asmus, Sulfur-Centered Reactive Intermediates in Chemistry and Biology, Springer, New York, 1991.
3. (a) A. L. Fluharty, in The Chemistry of the Thiol Group, part 2, ed. S. Patai, Wiley, New York, 1974, pp. 589-668;
4. b) M. Mikolajczyk, J. Drabowicz, A. Kielbasinski, in Methods of Organic Chemistry, 1995, vol.E21e, ch. 5, Georg Thime Verlag, Stuttgart.
5. (a) R. J. Parry, in Comprehensive Natural Products Chemistry, eds. D. Barton, K. Nakanishi, 1999, vol.1, p. 825, Pergamon Press, Oxford;
6. b) R. E. Gawley, J. Aube, in Principles of Asymmetric synthesis, Tetrahedron Organic Chemistry Series, 1996, vol. 14, p. 161, Oxford, Pergamon Press;
7. (c) R. Okazaki, in Organosulfur Chemistry, ed. P. Page, 1995, vol.1, p. 225, Academic Press, London;
8. d) Q. L. Zhou and A. Pfaltz, Tetrahedron, 1994, 50, 4467;
9. (e) J. C. Anderson and M. Harding, Chem. Commun., 1998, 393, and references therein;
10. f) C. E. Aroyan and S. J. Miller, J. Am. Chem. Soc. 2007, 129, 256;
11. g) S. Fanjul, A. N. Hulme and J. W. White, Org. Lett., 2006, 8, 4219.
12. (a) T. Kondo and T.-A. Mitsudo, Chem. Rev., 2000, 100, 3205;
13. b) M. Sibi and S. Manyem, Tetrahedron, 2000, 56, 8033.
14. P. Perlmutter, Conjugate Addition Reactions in Organic Syntheses, 1992, Pergamon Press.
15. (a) M.-C. Chu, S. Gao, S. Sastry, C.-W. Kuo, C. Lu, J.-T. Liu and C.-F. Yao, Tetrahedron, 2007, 63, 1863, and references therein;
16. b) G. L. Khatik, R. Kumar and A. K. Chakraborti, Org. Lett., 2006, 8, 2433;
17. (c) B. Movassagh and P. Shaygan, ARKIVOC, 2006, XII, 130;
18. d) T. C. Wabnitz, J.-Q. Yuand J. B. Spencer, Chem.-Eur. J., 2004, 10, 484;
19. (e) M. Meciarova and S. Toma, Lett. Org. Chem. 2006, 3, 794.
20. (a) H. Pracejus, F.-W. Wilke and K. Hanemann, J. Prakt. Chem. 1977, 319, 219;
21. b) H. Wynberg and R. Helder, Tetrahedron Lett., 1975, 16, 4057;
22. (c) N. Kobayashi and K. Iwai, J. Org. Chem. 1981, 46, 1823;
23. d) T. Mukaiyama, A. Ikegawa and K. Suzuki, Chem. Lett., 1981, 165.
24. (a) P. McDaid, Y. Chen and L. Deng, Angew. Chem. Int. Ed., 2002, 41, 338;
25. b) D. Leow, S. Lin, S. K. Chittimalla, X. Fu and C.-H. Tan, Angew. Chem. Int. Ed., 2008, 47, 5641;
26. (c) Y. Liu, B. Sun, B. Wang, M. Wakem and L. Deng, J. Am. Chem. Soc. 2009, 131, 418, and references therein.
27. (a) G Manickam and G Sundararajan, Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36, 516;
28. (b) G. Manickam and G Sundararajan, Tetrahedron: Asymmetry, 1997, 8, 2271;
29. (c) G. Manickam and G. Sundararajan, Tetrahedron, 1999, 55, 2721;
30. (d) G. Sundararajan and N. Prabagaran, Org. Lett., 2001, 3, 389;
31. (e) N. Prabagaran and G. Sundararajan, Tetrahedron: Asymmetry, 2002 ,13, 1053;
32. (f) N. Prabagaran, S. Abraham and G. Sundararajan, ARKIVOC, 2002, VII, 212.
33. (a) E. Emori, T. Arai, H. Sasai and M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 4043;
34. b) E. Emori, T. lida and M. Shibasaki, J. Org. Chem. 1999, 64, 5318;
35. (c) D. Sawada, M. Kanai and M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 10521.
36. (a) S. Narasimhan and S. Velmathi, Synth. Commun., 2002, 32, 3791;
37. b) S. Narasimhan and S. Velmathi, Molecules, 2003, 8, 256;
38. (c) S. Narasimhan, S. Swarnalakshmi and S. Velmathi, Tetrahedron: Asymmetry, 2003, 14, 113.
39. (a) M. Saito, M. Nakajima and S. Hashimoto, Chem. Commun., 2000, 1851;
40. b) M. Saito, M. Nakajima and S. Hashimoto, Tetrahedron, 2000, 56, 9589.
41. G. Kumaraswamy, M. N. V. Sastry and N. Jena, Tetrahedron Lett., 2001, 42, 8515.
42. T. Kumamoto, S. Aoki, M. Nakajima and K. Koga, Tetrahedron: Asymmetry, 1994, 5, 1431.
43. (a) K. Nishimura, M. Ono, Y. Nagaoka and K. Tomioka, J. Am. Chem. Soc. 1997, 119, 12974;
44. b) K. Tomioka, M. Okuda, K. Nishimura, S. Manabe, M. Kanai, Y. Nagaoka and K. Koga, Tetrahedron Lett., 1998, 39, 2141;
45. (c) K. Nishimura, M. Ono, Y. Nagaoka and K. Tomioka, Angew. Chem. Int. Ed., 2001, 40, 440;
46. d) K. Nishimura and K. Tomioka, J. Org. Chem. 2002, 67, 431;
47. (e) K. Nishimura and K. Tomioka, Yakugaku Zasshi, 2003, 123, 9.
48. (a) S. Kobayashi, C. Ogawa, M. Kawamura and M. Sugiura, Synlett, 2001, 983;
49. b) K. Matsumoto, A. Watanabe, T. Uchida, K. Ogi and T. Katsuki, Tetrahedron Lett., 2004, 45, 2385;
50. (c) S. J. Sauerland, E. Kiljunen and A. M. Koskinen, Tetrahedron Lett., 2006, 47, 1291.
51. (a) N. N. Joshi and S. C. Jha, ARKIVOC, 2002, VII, 167;
52. (b) D. Enders, K. Luttgen and A. Narine, Synthesis, 2007, 959.
53. M. E. Bruin and E. P. Kündig, Chem. Commun., 1998, 2635.
54. (a) E. P. Kündig, C. M. Saudan and G. Bernardinelli, Angew. Chem. 1999, 111, 1297;
55. E. P. Kündig, C. M. Saudan and G. Bernardinelli, Angew. Chem. Int. Ed., 1999, 38, 1219;
56. b) E. P. Kündig, M. C. Saudan, V. Alezra, F. Viton and G. Bernardinelli, Angew. Chem. 2001, 113, 4613;
57. E. P. Kündig, M. C. Saudan, V. Alezra, F. Viton and G. Bernardinelli, Angew. Chem. Int. Ed., 2001, 40, 4481;
58. (c) E. P. Kündig, C. M. Saudan and F. Viton, Adv. Synth. Catal., 2001, 343, 51;
59. d) P. G. A. Kumar, P. S. Pregosin, M. Vallet, G. Bernardinelli, R. F. Jazzar, F. Viton and E. P. Kündig, Organometallics, 2004, 23, 5410;
60. e) V. Alezra, G. Bernardinelli, C Corminboeuf, U. Frey, E. P. Kündig, A. E. Merbach, C. M. Saudan, F. Viton and J. Weber, J. Am. Chem. Soc. 2004, 126, 4843.
61. (a) F. Viton, G. Bernardinelli and E. P. Kündig, J. Am. Chem. Soc. 2002, 124, 4968;
62. b) A. Bãdoiu, Y. Brinkmann, F. Viton and E. P. Kündig, Pure Appl. Chem. 2008, 80, 1013;
63. (c) A. Bädoiu, G. Bernardinelli, J. Mareda, E. P. Kündig and F. Viton, Chem.-Asian J., 2008, 3, 1298;
64. (d) A. Bãdoiu, G. Bernardinelli, J. Mareda, E. P. Kündig and F. Viton, Chem.-Asian J., 2009, 4, 1021
65. (this article corrects Chem.-Asian J., 2008, 3, 1298).
66. Y. Brinkmann, J. M. Reniguntala, R. Jazzar, G. Bernardinelli and E. P. Kündig, Tetrahedron, 2007, 63, 8413.
67. J. Rickerby, M. Vallet, G. Bernardinelli, F. Viton and E. P. Kündig, Chem.-Eur. J., 2001, 13, 3354.
68. (a) K. J. Corvy and C. J. Helal, Tetrahedron Lett., 1995, 36, 9153;
69. b) A. B. Northrup and D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
70. (c) J. M. Hawkins, M. Nambu and S. Loren, Org. Lett., 2003, 5, 4293;
71. d) D. Carmona, M. P. Lamata, F. Viguri, R. Rodriguez, L. A. Oro, F. J. Lahoz, A. I. Baiana, T. Tejero and P. Merino, J. Am. Chem. Soc. 2005, 127, 13386;
72. (e) D. Carmona, M. P. Lamata, F. Viguri, J. Ferrer, N. Garcia, F. J. Lahoz, M. L. Martin and L. A. Oro, Eur. J. Inorg. Chem. 2006, 3155;
73. f) R. Gordillo and K. N. Houk, J. Am. Chem. Soc. 2006, 128, 3543.
74. See the electronic supplementary information for general experimental information, a complete table of solvent and temperature optimization, full experimental procedures and characterization data for all compounds, and a discussion on the X-ray structure of 22. See DOI: 10.1039/b918877k.
75. (a) X. Lu and L. Deng, Angew. Chem. Int. Ed., 2008, 47, 7710;
76. b) F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti and P. Melchiorre, Angew. Chem. Int. Ed., 2008, 47, 8703;
77. (c) D. R. Li, A. Muruganand J. R. Falck, J. Am. Chem. Soc. 2008, 130, 46;
78. d) J. Alemán, A. Milelli, S. Cabrera, E. Reyes and K. A. Jergensen, Chem.-Eur. J., 2008, 14, 10958.
79. (a) B. Dmuchovsky, B. D. Vineyard and F. B. Zienty, J. Am. Chem. Soc. 1964, 86, 2874;
80. b) H. Hiemstra and H. Wynberg, J. Am. Chem. Soc, 1981, 103, 417.
81. V. van Axel Castelli, A. Dalla Cort and L. Mandolini, J. Am. Chem. Soc , 1998, 120, 12688.
82. 31P NMR spectra. Analyses were carried out on a Bruker Avance 500 spectrometer.