Practical preparation of N-(1-alkynyl)sulfonamides and their synthetic utility in titanium alkoxide-mediated coupling reactions

Tetrahedron

Volumn 62, Issue 16, 2006, Pages 3896-3916

  Hirano, Shuji ^a   Fukudome, Yasuhiro ^a   Tanaka, Ryoichi ^a   Sato, Fumie ^a   Urabe, Hirokazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkynylation; Copper catalyst; Enamide; Sulfonamides; Titanacycle; Titanium alkoxide; Ynamide

Indexed keywords

ACETYLENE; ALDEHYDE DERIVATIVE; ALIPHATIC COMPOUND; ALKENE; N (1 ALKYNYL)SULFONAMIDE DERIVATIVE; SULFONAMIDE; TITANIUM; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALKYNYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIASTEREOISOMER; HYDROLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33645358897     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.080     Document Type: Article

References (81)

1. Trost, B. M., Fleming, I., Eds.; Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vols. 1-7.
2. For applications of (1-alkynyl)amine derivatives in these reactions, see: Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430.
3. Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272-7276.
4. Witulski, B.; Gößmann, M. Synlett 2000, 1793-1797.
5. Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
6. Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803-805.
7. Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417-2420.
8. Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353-9358.
9. Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509-1511.
10. Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681-3684.
11. Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002.
12. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130.
13. Negishi, E. In Trost, B. M., Fleming, I., Eds.; Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184.
14. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058.
15. (a) Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; pp 319-354.
16. (b) Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784.
17. (c) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835-2886.
18. (d) Eisch, J. J. J. Organomet. Chem. 2001, 617-618, 148-157.
19. (e) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834.
20. Acetylenic esters and amides: Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014-10027.
21. Urabe, H.; Nakajima, R.; Sato, F. Org. Lett. 2000, 2, 3481-3484.
22. Chloroacetylene: Averbuj, C.; Kaftanov, J.; Marek, I. Synlett 1999, 1939-1941.
23. Alkoxyacetylene: Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788-2796.
24. Sulfur-functionalized acetylenes: Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498.
25. Pagenkopf, B. L.; Lund, E. C.; Livinghouse, T. Tetrahedron 1995, 51, 4421-4438.
26. Kemp, M. I.; Whitby, R. J.; Coote, S. J. Synthesis 1998, 557-568.
27. Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925-7926.
28. Suzuki, D.; Nobe, Y.; Watai, Y.; Tanaka, R.; Takayama, Y.; Sato, F.; Urabe, H. J. Am. Chem. Soc. 2005, 127, 7474-7479.
29. Phosphorus-functionalized acetylene: Quntar, A. A. A.; Baum, O.; Shibli, A.; Dembitsky, V. M.; Srebnik, M. Angew. Chem., Int. Ed. 2003, 42, 4777-4779.
30. Portions of this work were already communicated. (a) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67-70.
31. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727-729.
32. Tanaka, R.; Yuza, A.; Watai, Y.; Suzuki, D.; Takayama, Y.; Sato, F.; Urabe, H. J. Am. Chem. Soc. 2005, 127, 7774-7780.
33. For a review on (1-alkynyl)amine derivatives, see: Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455-1475.
34. Zificsak, C A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575-7606.
35. Himbert, G In Kropf, H., Schaumann, E., Eds. 4th ed.; Houben-Weyl Methods of Organic Chemistry; Thieme: Stuttgart, 1993; Vol. E15/3, pp 3267-3443.
36. Collard-Motte, J; Janousek, Z. Top. Curr. Chem. 1986, 130, 89-131.
37. Witulski, B; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492.
38. Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256.
39. Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879-1880.
40. Witulski, B.; Lumtscher, J.; Bergsträßer, U. Synlett 2003, 708-710.
41. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
42. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
43. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
44. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
45. Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
46. (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
47. During the course of our study that was communicated as Ref. 6b, the following report appeared: (b) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368-2369.
48. However, this paper described that the sulfonamides and sultams are sluggish substrates toward the alkynylation. Furthermore, after the completion of the preparation of our communication (Ref. 6b), alkynylation of a couple of sulfonamides in the presence of a stoichiometric amount of a copper salt was reported: (c) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011-4014.
49. For review, see: Liu, Z.; Takeuchi, Y. Heterocycles 2002, 56, 693-709. Optically active benzosultams are readily prepared according to this literature.
50. For review, see: Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241-1250.
51. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
52. Stereoselective preparation of tri-substituted enamides of the type 29-42, which have two different β-alkyl (and -silyl) substituents, appears quite difficult. To the contrary, tri-substituted enamides having the same two β-substituents have been reported. Meuzelaar, G. J.; van Vliet, M. C. A.; Neeleman, E.; Maat, L.; Sheldon, R. A. Liebigs Ann. Recl. 1997, 1159-1163.
53. Murai, T.; Kasai, Y.; Ishihara, H.; Kato, S. J. Org. Chem. 1992, 57, 5542-5545.
54. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697-6703.
55. Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145.
56. In addition, hydrolysis of the acetylene-titanium complexes 26 afforded (Z)-disubstituted enamides. For details, see Ref. 6a. For recent reports on the preparation of (E)- or (Z)-disubstituted enamides, see: Trost, B. M.; Surivet, J.-P. Angew. Chem., Int. Ed. 2001, 40, 1468-1471.
57. Fürstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955-3957.
58. Krompiec, S.; Pigulla, M.; Szczepankiewicz, W.; Bieg, T.; Kuznik, N.; Leszczynska-Sejda, K.; Kubicki, M.; Borowiak, T. Tetrahedron Lett. 2001, 42, 7095-7098.
59. Miniere, S.; Cintrat, J.-C. Synthesis 2001, 705-707.
60. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408.
61. Witulski, B.; Buschmann, N.; Bergsträßer, U. Tetrahedron 2000, 56, 8473-8480.
62. Alonso, D. A.; Alonso, E.; Nájera, C.; Yus, M. Synlett 1997, 491-492.
63. Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413-414.
64. Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443-1446.
65. Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
66. Mitchell, H. J.; Nelson, A.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1999, 1899-1914.
67. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
68. For synthetic application of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986.
69. Ferreri, C.; Palumbo, G.; Caputo, R. In Trost, B. M., Fleming, I., Eds.; Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172.
70. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; pp 195-282.
71. Chiral enones are a promising substrate for asymmetric conjugate addition. Alexakis, A. In Organocopper Reagents A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 159-173.
72. The most likely conformation in CDCl3 was suggested by NOE study of 1H NMR. See Ref. 6b.
73. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
74. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206.
75. For other reported preparations of 1-amino-1,3-butadiene derivatives, see: Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354 see also 8295.
76. Overman, L. E.; Taylor, G. F.; Petty, C. B.; Jessup, P. J. J. Org. Chem. 1978, 43, 2164-2167.
77. Yli-Kauhaluoma, J. T.; Ashley, J. A.; Lo, C.-H.; Tucker, L.; Wolfe, M. M.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 7041-7047.
78. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
79. Huang, Y.; Iwama, T.; Rawal, V. H. Org. Lett. 2002, 4, 1163-1166 and references cited therein.
80. For our previous effort to make non-functionalized or electron-deficient dienes, see: Hamada, Y.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342-7344.
81. For a recent reviews on enyne cyclization, see: Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.