Iron-promoted elimination of β-thioalkoxy alcohols. Olefination by coupling of a carbonyl group with a dithioacetal

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3663-3665

  Huang, Li Fu ^a   Chen, Chih Wei ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548541305     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701579f     Document Type: Article

References (64)

1. (a) Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 6th ed.; Wiley: Hoboken, 2007; pp 1534-1546.
2. (b) Bruckner, R. Advanced Organic Chemistry: Reaction Mechanisms; Harcourt: San Diego, 2002; pp 160-167.
3. (c) Concellón, J. M.; Rodríguez-Solla, H. Chem. Soc. Rev. 2004, 33, 599.
4. (d) Shinokubo, H.; Oshima, K. Synlett 2000, 322.
5. (a) Percy, J. M. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1 (Roberts, S. M., Ed.), pp 553-587.
6. (b) Piva, O. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Pergamon: Oxford, 2005; Vol. 1 (Cossy, J., Ed.), pp 586-600.
7. Corey, E. J.; Winter, A. E. J. Am. Chem. Soc. 1963, 85, 2677.
8. For a review, see: Wong, H. N. C.; Fok, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345.
9. For reviews, see: (a) Maercker, A. Org. React. 1965, 74, 270.
10. (b) Wadsworth, W. S. Org. React. 1977, 25, 73.
11. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
12. (d) Shen, Y.-C Acta Chim. Sin. 2000, 58, 253.
13. For reviews, see: (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
14. (b) Ager, D. J. Org. React. 1990, 38, 1.
15. (c) Barrett, A. G. M.; Hill, J. M.; Wallace, E. M.; Flygare, J. A. Synlett 1991, 764.
16. (d) van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc Rev. 2002, 31, 195.
17. For reviews, see: (a) Kocienski, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6 (Winterfeldt, E., Ed.), pp 975-1039.
18. (b) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563.
19. For reviews, see: (a) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357.
20. (b) Page, P. C. B.; van Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643.
21. (c) Yus, M.; Nájera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
22. (a) Denis, J. N.; Dumont, W.; Krief, A. Tetrahedron Lett. 1979, 20, 4111.
23. (b) Hoye, T. R.; Kurth, M. J. J. Org. Chem. 1980, 45, 3549.
24. (c) Shimagaki, M.; Shiokawa, M.; Sugai, K.; Teranaka, T.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1988, 29, 659.
25. (d) Chevrie, D.; Lequeux, T.; Pommelet, J.-C. Org. Lett. 1999, 1, 1539.
26. For a review, see: Luh, T.-Y.; Ni, Z.-J. Synthesis 1990, 89.
27. Examples on stoichiometric β-heteroatom elimination reactions: (a) Rosenblum, M. Pure Appl. Chem. 1984, 56, 129.
28. (b) Daves, G. D., Jr. Acc. Chem. Res. 1990, 23, 201.
29. Examples on catalytic β-heteroatom elimination reactions: (a) Henry, P. M. Acc Chem. Res. 1973, 6, 16.
30. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286.
31. (c) Shi, X.; Luh, T.-Y. Organometallics 1990, 9, 3019.
32. (d) Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
33. (e) Sen, A.; Lin, M.; Kao, L.-C.; Huston, A. C. J. Am. Chem. Soc. 1992, 114, 6385.
34. (f) Shiu, L.-L.; Yu, C.-C; Wong, K.-T.; Chen, B.-L.; Cheng, W.-L.; Yuan, T.-M.; Luh, T.-Y. Organometallics 1993, 12, 1018.
35. (g) Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
36. (h) Zhu, G.; Lu, X. Organometallics 1995, 14, 4899.
37. (a) Ikehara, H.; Tanimoto, S.; Oida, T. J. Chem. Soc., Perkin Trans. 1 1984, 1223.
38. (b) Krief, A.; Kenda, B.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 2509.
39. For a recent review, see: Luh, T.-Y.; Lee, C.-F. Eur. J. Org. Chem. 2005, 3875.
40. (a) Tseng, H.R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 8685.
41. (b) Tseng, H.-R.; Luh, T.-Y. J. Org. Chem. 1997, 62, 4568.
42. (c) Tseng, H.-R.; Lee, C.-F.; Yang, L.-M.; Luh, T.-Y. J. Org. Chem. 1999, 64, 8582.
43. (a) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-H.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992.
44. (b) Zhang, L.-Z.; Chen, C.-W.; Lee, C.-F.; Wu, C.-C.; Luh, T.-Y. Chem. Commun. 2002, 2336.
45. (c) Lee, C.-F.; Liu, C.-Y.; Song, H.-C.; Luo, S.-J.; Tseng, J.-C.; Tso, H.-H.; Luh, T.-Y. Chem. Commun. 2002, 2824.
46. (d) Liu, C.-Y.; Luh, T.-Y. Org. Lett. 2002, 4, 4305.
47. (e) Chou, C.-M.; Chen, W.-Q.; Chen, J.-H.; Tseng, J.-C.; Lee, C.-F.; Luh, T.-Y. Chem. Asian J. 2006, 7-2, 46.
48. (f) Tseng, J.-C.; Chen, J.-H.; Luh, T.-Y. Synlett. 2006, 1209.
49. (a) For a recent review, see: Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624.
50. (b) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686.
51. (c) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
52. (d) Beford, R. B.; Bruce, D. W.; Frost, R. M.; Goodby, J. W.; Hird, M. Chem. Commun. 2004, 2822.
53. (e) Dunet, G.; Knochel, P. Synlett 2006, 407.
54. (f) Dongol, K. G.; Koh, H.; Sau, M.; Chai, C. L. L. Adv. Synth. Catal. 2007, 349, 1015.
55. (a) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Lett. 1985, 26, 3595.
56. (b) Fiandanese, V.; Marchese, G.; Naso, F. Tetrahedron Lett. 1988, 29, 3587.
57. (c) Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J.-i. Org. Lett. 2005, 7, 1219.
58. (a) Alper, H.; Prince, T. L. Angew. Chem., Int. Ed. 1980, 79, 315.
59. (b) Alper, H.; Ripley, S.; Prince, T. L. J. Org. Chem. 1983, 48, 250.
60. (c) Alper, H.; Sibtain, F.; Haveling, J. Tetrahedron Lett. 1985, 24, 5329.
61. An excess amount of MeMgI (5 equiv) was necessary in order to drive the reaction to completeness.
62. The aliphatic-substituted propargylic dithioacetals 7 were conveniently obtained from the alkylation of the anion of the corresponding parent dithioacetals 10 (cf. Huang, L.-F.; Lee, C.-F.; Tseng, J.-C.; Luh, T.-Y. Synlett 2006, 3173). The details are described in the Supporting Information.
63. Wilson, S. R.; Georgiadis, G. M.; Khatri, H. N.; Bartmess, J. E. J. Am. Chem. Soc. 1980, 102, 3577.
64. Zhang, D.; Ready, J. M. J. Am. Chem. Soc. 2006, 128, 15050.