N-acylsulfonamide linker activation by Pd-catalyzed allylation

Organic Letters

Volumn 8, Issue 12, 2006, Pages 2483-2485

  He, Yi ^a   Wilkins, Jesse P ^a   Kiessling, Laura L ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; SULFONAMIDES;

EID: 33745517566     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060428o     Document Type: Article

References (36)

1. Recent reviews on linkers for SPOS: (a) James, I. W. Tetrahedron 1999, 55, 4855-4946.
2. b) Guillier, F.; Grain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157.
3. (c) Qiang, H.; Quan, L.; Zheng, B. Z. Prog. Chem. 2004, 16, 236-242.
4. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. Chem. Commun. 1971, 636-637.
5. Review on "safety-catch" linkers: Patek, M.; Lebl, M. Biopolymers 1998, 47, 353-363.
6. For a review on the N-acylsulfonamide linker, see the following: Heidler, P.; Link, A. Bioorg. Med. Chem. 2005, 13, 585-599.
7. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374.
8. Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689.
9. (a) Quaderer, R.; Hilvert, D. Org. Lett. 2001, 3, 3181-3184.
10. (b) Ollivier, N.; Behr, J. B.; El-Mahdi, O.; Blanpain, A.; Melnyk, O. Org. Lett. 2005, 7, 2647-2650.
11. (c) Zohrabi-Kalantari, V.; Heidler, P.; Larsen, T.; Link, A. Org. Lett. 2005, 7, 5665-5667.
12. (a) Hahn, M. E.; Muir, T. W. Trends Biochem. Sci. 2005, 30, 26-34.
13. (b) Dawson, P. E.; Muir, T. W.; Clarklewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
14. (c) Dawson, P. E.; Kent S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
15. (d) Kent, S. B. H. Annu. Rev. Biochem. 1988, 57, 957-989.
16. (a) Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2001, 3, 9-12.
17. (b) Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1941.
18. (c) Nilsson, B. L.; Hondal, R. J.; Soellner, M. B.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 5268-5269.
19. (d) He, Y.; Hinklin, R. J.; Chang, J.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
20. Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
21. Zohrabi-Kalanlari, V.; Heidler, P.; Larsen, T.; Link, A. Org. Lett. 2005, 7, 5665-5667.
22. (a) Pearson, R. G.; Songstad, J. J. Am. Chem. Soc. 1967, 89, 1827-1836.
23. (b) Ho, T.-L. Chem. Rev. 1975, 75, 1-20.
24. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965. 4387-4388.
25. Reviews on Pd-catalyzed allylation: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144-152.
26. (b) Godleski, S. A. In Comprehensive Organic Synthesis; Barton, S. D., Ollis, D. W., Eds.; Pergamon Press: New York, 1991; pp 585-661.
27. For a review on Pd-catalyzed allylation using allyl carbonates under neutral conditions: Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140-145.
28. (a) Bystrom, S. E.; Aslanian, R.; Backvall, J. E. Tetrahedron Lett. 1985, 26, 1749-1752.
29. (b) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.: Roglans, A. Tetrahedron 1998, 54, 14869-14884.
30. (a) Zasloff, M. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5449-5493.
31. (b) Zasloff, M.; Martin, B.; Chen, H. C. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 910-913.
32. (a) Dourtoglou, V.; Ziegler, J. C.; Gross, B. Tetrahedron Lett. 1978, 1269-1272.
33. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
34. (c) Lew, A.; Chamberlin, A. R. Bioorg. Med. Chem. Lett. 1999, 9, 3267-3272.
35. The amino acids used for the synthesis of peptides 4 and 5 were Fmoc-Ala-OH, Fmoc-Phe-OH, Fmoc-Gly-OH, Boc-Gly-OH (terminal Gly), Fmoc-His(Trt)-OH, Fmoc-Ile-OH, Fmoc-Lys(Boc)-OH, Fmoc-Leu-OH, and Fmoc-Ser(tBu)-OH.
36. a values of allylammonium and methylammonium are 9.47 and 10.67, respectively, from: Hall, H. K. J. Am. Chem. Soc. 1957, 79, 5441-5444. Differences in conformation or strain may also contribute to the observed reactivity differences.