Reactions of alkenes, alkynes, and alkoxyallenes with new polymer-supported electrophilic reagents

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2101-2104

  Monenschein, Holger ^a   Sourkouni Argirusi, Georgia ^a   Schubothe, Katherine M ^b   O'Hare, Thomas ^b   Kirschning, Andreas ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

^b WILLAMETTE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000940686     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991149m     Document Type: Article

References (51)

1. Reviews: (a) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1998, 1217-1239.
2. (b) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
3. (c) Hodge, P.; Sherringtom, D. C. In Polymer-Supported Reaction in Synthesis; Wiley: New York, 1990.
4. (d) Laszlo, P., Ed. In Preparative Chemistry using Supported Reagents; Academic: San Diego, 1987.
5. (a) Flynn, D. L.; Devraj, J. J. Parlow, Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50.
6. (b) Suto, M. J.; Gayo-Fung, L. M.; Palanki, M. S. S.; Sullivan, R. Tetrahedron 1998, 54, 4141-4150.
7. (c) Parlow, S. S. Tetrahedron Lett. 1996, 37, 5257-5260.
8. (d) Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. 1 1998, 3127-3130.
9. (e) Caldarelli, M.; Habermann, J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1999, 107-110.
10. Reviews: (a) Block, E.; Schwan, A. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 329-362.
11. (b) Rodriguez, J.; Dulcère, J.-P. Synthesis 1993, 1177-1205.
12. (a) Olah, G. A.; Li, X.; Wang, Q.; Prakash, G. K. S. Synthesis 1993, 693-699.
13. (b) Zajc, B.; Zupan, M. Tetrahedron 1989, 45, 7869-7878.
14. (c) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364-7369.
15. (a) Kirschning, A.; Plumeier, C.; Rose, L. Chem. Commun. 1998, 33-34.
16. (b) Hashem, Md. A.; Jung, A.; Ries, M.; Kirschning, A. Synlett 1998, 195-197.
17. (c) Kirschning, A.; Hashem, Md. A.; Monenschein, H.; Rose, L.; Schöning, K.-U. J. Org. Chem. 1999, 64, 2720-2722.
18. Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722; Angew. Chem., Int. Ed. Engl. 1999, 38, 2594-2596.
19. Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722; Angew. Chem., Int. Ed. Engl. 1999, 38, 2594-2596.
20. 2 (3x) and drying in vacuo afforded the light yellow reagents 3a and 3b or pink resin 3c.
21. (a) Doleschall, G.; Tóth, G. Tetrahedron 1980, 36, 1649-1665.
22. (b) Szántay, C.; Blaskó, G.; Bárcrczai-Beke, M.; Péchy, P.; Dörnei, G. Tetrahedron Lett. 1980, 21, 3509-3512.
23. (c) Matsuo, K.; Ishida, S.; Takuno, Y. Chem. Pharm. Bull. 1994, 42, 1149-1150.
24. (a) Mangoni, L.; Adinolfi, M.; Barone, G.; Parrilli, M. Tetrahedron Lett. 1973, 4485-4486.
25. (b) Mangoni, L.; Adinolfi, M.; Barone, G.; Parrilli, M. Gazz. Chim. Ital. 1975, 105, 377-383.
26. (c) Adinolfi, M.; Parrilli, M.; Barone, G.; Laonigro, G.; Mangoni, L. Tetrahedron Lett. 1976, 3661-3663.
27. (a) Birckenbach, L.; Goubeau, J.; Berninger, E. Ber. 1932, 65, 1339-1344.
28. (b) Woodward, R. B.; Brutcher, F. V., Jr. J. Am. Chem. Soc. 1958, 80, 209-211.
29. (c) Cambie, R. C.; Gash, D. M.; Rutledge, P. S.; Woodgate, P. D. J. Chem. Soc., Perkin Trans. 1 1977, 1157-1162.
30. (d) Barluenga, J.; Rodriguez, M. A.; Campos, P. J.; Asenio, G. J. Chem. Soc., Chem. Commun. 1987, 1491-1492.
31. (e) Georgoulis, C.; Valery, J. Bull. Soc. Chim. Fr. 1975, 1431-1432.
32. (f) Trainor, R. W.; Deacon, G. B.; Jackson, W. R.; Giunta, N. Aust. J. Chem. 1992, 45, 1265-1280.
33. (g) Bedekar, A. V.; Nair, K. B.; Soman, R. Synth. Commun. 1994, 24, 2299-2305.
34. 2 (3x), and the combined organic washings and filtrate were concentrated under reduced pressure. In some cases, further purification by column chromatography was necessary. Finally, the polymer was recycled to the halide form 1 by treatment with concentrated HBr or HI for 1 h at room temperature.
35. The assignment of the trans stereochemistry in 7-10 is based on the analogy to compounds 13 and 14 and the known preference for iodoacetoxylation of alkenes (see refs 9 and 10).
36. 3.
37. Diederich, F.; Stang, P. J. In Metal-catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
38. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
39. (b) Negishi, E.; Copéret, C.; Ma., S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
40. (c) Shibasaki, M.; Boden, C. O. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
41. (d) Mitchell, T. N. Synthesis 1992, 803-815.
42. (e) Farina, V. Pure Appl. Chem. 1996, 68, 73-78.
43. (a) Moriya, O.; Akawara, M.; Ueno, Y. Chem Lett. 1984, 1437-1438.
44. (b) Dulcère, J.-P.; Mihoubi, M. N.; Rodriguez, J. J. Chem. Soc., Chem. Commun. 1988, 237-239.
45. Alkynyl iodides can efficiently be transformed into the corresponding (Z)-vinyl iodides by diimine-promoted reduction: Mulzer, J., personal communication.
46. Selected examples of 1-alkinyl halides in transition metal catalyzed cross coupling reactions: (a) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. L. J. Am. Chem. Soc. 1978, 100, 2254-2256.
47. (b) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
48. (c) Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755-3757.
49. (d) Yamanoi, S.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1999, 40, 2793-2796.
50. Recently, polymer-supported (diacetoxyiodo)benzene was introduced by (a) Ley, S. V.; Thomas, A. W.; Finch, H. J. Chem. Soc., Perkin Trans. 1 1999, 669-671.
51. (b) Togo, H.; Nogami, G.; Yokoyama, M. Synlett 1998, 534-536.