α-trialkylsilyl amino acid stability

Organic Letters

Volumn 7, Issue 4, 2005, Pages 665-668

  Liu, Guodong ^a   Sieburth, Scott McN ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; AMINO ACID; CARBON; CARBONYL DERIVATIVE; ESTER; METHYL GROUP; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; LIPOPHILICITY; METHANOLYSIS; TEMPERATURE DEPENDENCE;

ALKYLATION; AMINO ACIDS; DRUG STABILITY; METHANE; MODELS, MOLECULAR; SILANES; SILICON;

EID: 14844341357     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047508h     Document Type: Article

References (48)

1. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. van Maarsveen, J. H.; Back, J. W. Angew. Chem., Int. Ed. 2003, 42, 5926-5928. Rinaldi, A. EMBO Rep. 2004, 5, 336-339.
2. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. van Maarsveen, J. H.; Back, J. W. Angew. Chem., Int. Ed. 2003, 42, 5926-5928. Rinaldi, A. EMBO Rep. 2004, 5, 336-339.
3. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. van Maarsveen, J. H.; Back, J. W. Angew. Chem., Int. Ed. 2003, 42, 5926-5928. Rinaldi, A. EMBO Rep. 2004, 5, 336-339.
4. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652. Wang, L.; Schultz, P. G. J. Chem. Soc., Chem. Commun. 2002, 1-11. van Maarsveen, J. H.; Back, J. W. Angew. Chem., Int. Ed. 2003, 42, 5926-5928. Rinaldi, A. EMBO Rep. 2004, 5, 336-339.
5. Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
6. Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495. Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591.
7. Birkofer, L.; Ritter, A. Angew. Chem. 1956, 68, 461-462. Tacke, R.; Handmann, V. I. Organometallics 2002, 21, 2619-2626.
8. Birkofer, L.; Ritter, A. Angew. Chem. 1956, 68, 461-462. Tacke, R.; Handmann, V. I. Organometallics 2002, 21, 2619-2626.
9. Frankel, M.; Shenhar, A.; Gertner, D.; Zilkha, A. Israel J. Chem. 1968, 6, 921-926.
10. Handmann, V. I.; Mergel, M.; Tacke, R. Z. Naturfursch. B. 2000, 55, 133-138. Vivet, B.; Cavelier, F.; Martinez, J. Eur. J. Org. Chem. 2000, 807-811.
11. Handmann, V. I.; Mergel, M.; Tacke, R. Z. Naturfursch, B. 2000, 55, 133-138. Vivet, B.; Cavelier, F.; Martinez., J. Eur. J. Org. Chem. 2000, 807-811.
12. Cavelier, F.; Vivet, B.; Martinez, J.; Aubry, A.; Didierjean, C.; Vicherat, A.; Marraud, M. J. Am. Chem. Soc. 2002, 124, 2917-2923.
13. Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547-1550.
14. (a) Sieburth, S. McN.; Somers, J. J.; O'Hare, H. K.; Hewitt, G. W. Appl. Organomet. Chem. 1997, 11, 337-343.
15. (b) Bolm, C.; Kusyan, A.; Drauz, K.; Günther, K.; Raabe, G. Angew. Chem., Int. Ed. 2000, 39, 2288-2290.
16. (c) Chen, J.-X.; Tunge, J. A.; Norton, J. R. J. Org. Chem. 2002, 67, 4366-4369.
17. (d) Liu, G.; Sieburth, S. McN. Org. Lett. 2003, 5, 4677-4679.
18. Noll, J. E.; Daubert, B. F.; Speier, J. L. J. Am. Chem. Soc. 1951, 73, 3871-3873. Sommer, L. H.; Rockett, J. J. Am. Chem. Soc. 1951, 73, 5130-5134.
19. Noll, J. E.; Daubert, B. F.; Speier, J. L. J. Am. Chem. Soc. 1951, 73, 3871-3873. Sommer, L. H.; Rockett, J. J. Am. Chem. Soc. 1951, 73, 5130-5134.
20. Landais, Y. In Organometallics; Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2000; Vol. 4, pp 757-771. Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
21. Landais, Y. In Organometallics; Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2000; Vol. 4, pp 757-771. Larson, G. L. Adv. Silicon Chem. 1996, 3, 105-271.
22. Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1995, 51, 10653-10662. Review: Bommarius, A. S.; Schwarm, M.; Stingl, K.; Kottenhahn, M.; Huthmacher, K.; Drauz, K. Tetrahedron: Asymmetry 1995, 6, 2851-2888.
23. Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1995, 51, 10653-10662. Review: Bommarius, A. S.; Schwarm, M.; Stingl, K.; Kottenhahn, M.; Huthmacher, K.; Drauz, K. Tetrahedron: Asymmetry 1995, 6, 2851-2888.
24. Lyu, P. C.; Sherman, J. C.; Chen, A.; Kallenbach, N. R. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 5317-5320.
25. Examples include: (a) Atazanavir: Havlir, D. V.; O'Marro, S. D. Clin. Infect. Disease 2004, 38, 1599-1604. (b) NT69L: Boules, M.; Fredrickson, P.; Richelson, E. Life Sci. 2003, 73, 2785-2792. (c) Marimastat: Shepherd, F. A.; Giaccone, G.; Seymour, L.; Debruyne, C.; Bezjak, A.; Hirsh, V.; Smylie, M.; Rubin, S.; Martins, H.; Lamont, A.; Krzakowski, M.; Sadura, A.; Zee, B. J. Clin. Oncol. 2002, 20, 4434-4439.
26. Examples include: (a) Atazanavir: Havlir, D. V.; O'Marro, S. D. Clin. Infect. Disease 2004, 38, 1599-1604. (b) NT69L: Boules, M.; Fredrickson, P.; Richelson, E. Life Sci. 2003, 73, 2785-2792. (c) Marimastat: Shepherd, F. A.; Giaccone, G.; Seymour, L.; Debruyne, C.; Bezjak, A.; Hirsh, V.; Smylie, M.; Rubin, S.; Martins, H.; Lamont, A.; Krzakowski, M.; Sadura, A.; Zee, B. J. Clin. Oncol. 2002, 20, 4434-4439.
27. Examples include: (a) Atazanavir: Havlir, D. V.; O'Marro, S. D. Clin. Infect. Disease 2004, 38, 1599-1604. (b) NT69L: Boules, M.; Fredrickson, P.; Richelson, E. Life Sci. 2003, 73, 2785-2792. (c) Marimastat: Shepherd, F. A.; Giaccone, G.; Seymour, L.; Debruyne, C.; Bezjak, A.; Hirsh, V.; Smylie, M.; Rubin, S.; Martins, H.; Lamont, A.; Krzakowski, M.; Sadura, A.; Zee, B. J. Clin. Oncol. 2002, 20, 4434-4439.
28. Kitching, W.; Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153-5156. Penman, K. G.; Kitching, W.; Adcock, W. J. Org. Chem. 1989, 54, 5390-5391. Arnason, I.; Kvaran, A.; Jonsdottir, S.; Gudnason, P. I.; Oberhammer, H. J. Org. Chem. 2002, 67, 3827-3831.
29. Kitching, W.; Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153-5156. Penman, K. G.; Kitching, W.; Adcock, W. J. Org. Chem. 1989, 54, 5390-5391. Arnason, I.; Kvaran, A.; Jonsdottir, S.; Gudnason, P. I.; Oberhammer, H. J. Org. Chem. 2002, 67, 3827-3831.
30. Kitching, W.; Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153-5156. Penman, K. G.; Kitching, W.; Adcock, W. J. Org. Chem. 1989, 54, 5390-5391. Arnason, I.; Kvaran, A.; Jonsdottir, S.; Gudnason, P. I.; Oberhammer, H. J. Org. Chem. 2002, 67, 3827-3831.
31. White, D. P.; Anthony, J. C.; Oyefeso, A. O. J. Org. Chem. 1999, 64, 7707-7716.
32. The ethyidimethylsilyl group is not found in: (a) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York. 2000. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999. (c) Activating Groups and Protecting Groups; Pearson, A. J., Roush, W. R., Eds.; John Wiley & Sons: New York, 1999. (d) Hanson, J. R. Protecting Groups in Organic Synthesis; Blackwell Science: Malden, MA, 1999.
33. The ethyidimethylsilyl group is not found in: (a) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York. 2000. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999. (c) Activating Groups and Protecting Groups; Pearson, A. J., Roush, W. R., Eds.; John Wiley & Sons: New York, 1999. (d) Hanson, J. R. Protecting Groups in Organic Synthesis; Blackwell Science: Malden, MA, 1999.
34. The ethyidimethylsilyl group is not found in: (a) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York. 2000. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999. (c) Activating Groups and Protecting Groups; Pearson, A. J., Roush, W. R., Eds.; John Wiley & Sons: New York, 1999. (d) Hanson, J. R. Protecting Groups in Organic Synthesis; Blackwell Science: Malden, MA, 1999.
35. The ethyidimethylsilyl group is not found in: (a) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York. 2000. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999. (c) Activating Groups and Protecting Groups; Pearson, A. J., Roush, W. R., Eds.; John Wiley & Sons: New York, 1999. (d) Hanson, J. R. Protecting Groups in Organic Synthesis; Blackwell Science: Malden, MA, 1999.
36. Miyazaki, H.; Ishibashi, M.; Itoh, M.; Nambara, T. Chem. Pharm. Bull. 1975, 23, 3033-3035.
37. Otter, J. C.; Adamson, C. L.; Yoder, C. H.; Rheingold, A. L. Organometallics 1990, 9, 1557-1562.
38. Käppler, K.; Scheim, U.; Rühlmann, K.; Porzel, A. J. Organomet. Chem. 1992, 441, 15-25.
39. Shimizu, N.; Takesue, N.; Yamamoto, A.; Tsutsumi, T.; Yasuhara, S.; Tsuno, Y. Chem. Lett. 1992, 1263-1266.
40. Kozuka, S.; Kitamura, T.; Kobayashi, N.; Ogino, K. Bull. Chem. Soc. Jpn. 1979, 52, 1950-1952. Scheim, U.; Grosse-Ruyken, H.; Rühlmann, K.; Porzel, A. J. Organomet. Chem. 1985, 293, 29-36.
41. Kozuka, S.; Kitamura, T.; Kobayashi, N.; Ogino, K. Bull. Chem. Soc. Jpn. 1979, 52, 1950-1952. Scheim, U.; Grosse-Ruyken, H.; Rühlmann, K.; Porzel, A. J. Organomet. Chem. 1985, 293, 29-36.
42. Bilda, S.; Lange, D.; Popowski, E.; Kelling, H. Z. Anorg. Allg. Chem. 1987, 550, 186-194.
43. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. Giuseppone, N.; Van De Weghe, P.; Mellah, M.; Collin, J. Tetrahedron 1998, 54, 13129-13148.
44. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078. Giuseppone, N.; Van De Weghe, P.; Mellah, M.; Collin, J. Tetrahedron 1998, 54, 13129-13148.
45. Sakurai, H.; Hosomi, A.; Kumada, M. J. Org. Chem. 1969, 34, 1764-1768. Sakurai, H.; Hayashi, N.; Kumada, M. J. Organomet. Chem. 1969, 78, 351-354.
46. Sakurai, H.; Hosomi, A.; Kumada, M. J. Org. Chem. 1969, 34, 1764-1768. Sakurai, H.; Hayashi, N.; Kumada, M. J. Organomet. Chem. 1969, 78, 351-354.
47. Lorsbach, B. A.; Prock, A.; Giering, W. P. Organometallics 1995, 14, 1694-1699.
48. Leigh, W. J.; Boukherroub, R.; Kerst, C. J. Am. Chem. Soc. 1998, 120, 9504-9512.