Carbosilane dendrimeric carbodiimides: Site isolation as a lactamization tool

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 1851-1860

  Amore, Alessia ^a   Van Heerbeek, Rieko ^a   Zeep, Niek ^b   Van Esch, Jan ^b   Reek, Joost N H ^a   Hiemstra, Henk ^a   Van Maarseveen, Jan H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; HYDROGENATION; SILANES; SYNTHESIS (CHEMICAL);

CARBODIIMIDES; HOMODIKETOPIPERAZINES; HYDROSILYLATION;

DENDRIMERS;

ALLYL CHLORIDE; ALLYLMAGNESIUM BROMIDE; CARBOSILANE DERIVATIVE; CHLORINE DERIVATIVE; CYANAMIDE; DENDRIMER; MAGNESIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; GRIGNARD REACTION; HYDROGEN BOND; HYDROGENATION; HYDROSILYLATION; INFRARED SPECTROSCOPY; ISOLATION PROCEDURE; LACTAMIZATION; REACTION ANALYSIS;

EID: 33644651272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052027c     Document Type: Article

References (66)

1. (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Wedges: Concept, Synthesis and Application; Wiley-VCH: Weinheim, 2001.
2. (b) Dendrimers and Other Dendritic Polymers: Fréchet, J. M. J., Tomalia, D. A., Eds.: Wiley: Chichester, 2001.
3. (a) Hawker, C. J.; Wooley, L. K.; Fréchet, J. M. J. J. Am. Chem. Soc. 1993, 115, 4375-4376.
4. (b) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
5. Muller, C.; Ackerman, L.; Reek, J. N. H.; Kamer, P. C. J.; Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2004, 126, 14960-14963.
6. For recent reviews, see: (a) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
7. (b) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717-3756.
8. (c) Preston, A. C.; Klein Gebbink, R. J. M.; van Koten, G. J. Organomet. Chem. 2004, 24, 4016-4054.
9. Reviews: (a) Klein Gebbink, R. J. M.; Kruithof, C. A.; van Klink, G. P. M.; van Koten, G. Mol. Biotechnol. 2002, 90, 183-193.
10. (b) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717-3756.
11. Kim, R. M.; Manna, M.; Hutchins, S. M.; Griffin, P. R.; Yates, N. A.; Bernik, A. M.; Chapman, K. T. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10012-10017.
12. (a) Hovestad, N. J.; Jastrzebski, J. T. B. H.; van Koten, G. Polym. Mater. Sci. Eng. 1999, 80, 53-54.
13. (b) Hovestad, N. J.; Ford, A.; Jastrzebski, J. T. B. H.; van Koten, G. J. Org. Chem. 2000, 65, 6338-6344.
14. Le Nôtre, J.; Firet, J. J.; Sliedregt, L. A. J. M.; van Steen, B. J.; van Koten, G.; Klein Gebbink, R. J. M. Org. Lett. 2005, 7, 363-366.
15. (a) Nubbemeyer, U. Top. Curr. Chem. 2001, 216, 126-193.
16. (b) Schmidt, U.; Langner, J. J. Pept. Res. 1997, 49, 2481-2495.
17. (a) Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. J. Chem. Soc., Perkin Trans. 1 2001, 471-484.
18. (b) Sewald, N.; Jakubke, H.-D. Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, 2002.
19. For a recent review about cyclization methodologies, see: Davies, J. S. J. Pept. Sci. 2003, 9, 471-501.
20. Alsina, J.; Jensen, K. J.; Albericio, F.; Barany, G. Chem.-Eur. J. 1999, 5, 2787.
21. (a) Meutermans, W. D. F.; Golding, S. W.; Bourne, G. T.; Miranda, L. P.; Dooley, M. J.; Alewood, P. F.; Smythe, M. L. J. Am. Chem. Soc. 1999, 121, 9790-9796.
22. (b) Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2003, 1, 1830-1832.
23. (c) Meutermans, W. D. F.; Bourne, G. T.; Golding, S. W.; Horton, D. A.; Campitelli, M. R.; Craik, D.; Scanlon, M.; Smythe, M. L. Org. Lett. 2003, 7, 2711-2714.
24. David, O.; Meester, W.; Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem., Int. Ed. 2003, 42, 4373-4375.
25. (a) Bordusa, F. ChemBioChem 2001, 2, 99-107.
26. (b) Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658.
27. (c) Sieber, S. A.; Tao, J.; Walsh, C. T.; Marahiel, M. A. Angew. Chem., Int. Ed. 2004, 43, 493-498.
28. (a) van der Made, A. Chem. Commun. 1992, 1400-1401.
29. (b) van der Made, A. Adv. Mater. 1993, 5, 466-467.
30. (c) Roovers, J.; Toporowski, P. M.; Zhou, L. Polym. Prepr. 1992, 182-183.
31. (d) Zhou, L.; Roovers, J. Macromolecules 1993, 26, 963-968.
32. (e) Muzafarov, A. M.; et al. Polym. Sci. 1993, 35, 1575-1580.
33. (a) Kim, C.; Park, E.; Kang, E. J. Korean Chem. Soc. 1995, 39, 799-805.
34. (b) Kim, C.; Park, E.; Kang, E. Bull. Korean Chem. Soc. 1996, 17, 419-424.
35. (c) Kim, C.; An, K. Bull. Korean Chem. Soc. 1997, 18, 164-170.
36. (d) Kim, C.; Sung, D.-D.; Chung, D.; Park, E.; Kang, E. J. Korean Chem. Soc. 1995, 39, 789-798.
37. (e) Seyferth, D.; Kugita, T.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1995, 14, 5362-5366.
38. (f) Gossage, R. A.; Muñoz-Martínez, E.; Frey, H.; Burgath, A.; Lutz, M.; Spek, A. L.; van Koten, G. Chem.-Eur. J. 1999, 1, 2191-2197.
39. van Heerbeek, R.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 7127-7130.
40. Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 1999, 1119-1120.
41. Gossage, R. A.; Muñoz-Martínez, E.; Frey, H.; Burgath, A.; Lutz, M.; Spek, A. L.; van Koten, G. Chem.-Eur. J. 1999, 5, 2191-2196.
42. Botman, P. N. M.; Amore, A.; van Heerbeek, R.; Black, J. W.; Hiemstra, H.; Reek, J. N. H.; van Maarseveen, J. H. Tetrahedron Lett. 2004, 45, 5999-6002.
43. For an extensive study on the Pt(0)-catalyzed hydrosilylation, see: Stein, J.; Lewis, L. N.; Gao, Y.; Scott, R. A. J. Am. Chem. Soc. 1999, 121, 3693 and references therein.
44. Iovel, I. G.; Goldberg, Y. S.; Shymanska, M. V.; Lukevics, E. Organometallics 1987, 6, 1410-1413.
45. de Groot, D. Ph.D. Thesis, University of Amsterdam, The Netherlands, 2001.
46. (a) Lorenz, K.; Mülhaupt, R.; Frey, H.; Rapp, H.; Mayer-Posner, F. J. Macromolecules 1995, 28, 6657-6661.
47. (b) Krska, S. W.; Seyferth, D. J. Am. Chem. Soc. 1998, 120, 3604-3612.
48. De Backer, S.; Prinzie, Y.; Verheijen, W.; Smet, M.; Desmedt, K.; Dehaen, W.; De Schryver, F. C. J. Phys. Chem. A 1998, 102, 5451-5155.
49. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646.
50. Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 8, 763-764.
51. Review: Mikolajczyk, M.; Kielbasinski, P. Tetrahedron 1981, 37, 233-284.
52. (a) Mohmeyer, N.; Schmidt, H-W. Chem.-Eur. J. 2005, 11, 863-873.
53. (b) Lottie, F.; Boileau, S.; Boutellier, L. Chem.-Eur. J. 2003, 9, 3008-3014.
54. Dobrowolski, J. Cz.; Jamroz, M. H.; Mazurek, A. P. Vib. Spectrosc. 1994, 8, 53-60.
55. (a) Hanasuba, K.; Yamada, M.; Kimura, M.; Shirai, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1949-1951.
56. (b) Schoonbeck, F. S.; de Loos, M.; Kooijman, H.; Kellogg, R. M.; Feringa, B. L. Chem.-Eur. J. 1999, 5, 937-950.
57. Haushalter, K. A.; Lau, J.; Roberts, J. D. J. Am. Chem. Soc. 1996, 118, 8891-8896.
58. (a) Katritzky, A. R.; Jiang, J.; Urogdi, L. Synthesis 1990, 565-567.
59. (b) Ding, M-W.; Tu, H.-Y.; Liu, Z.-J. Synth. Commun. 1997, 27, 3657-3662.
60. (c) Heras, M.; Ventura, M.; Linden, A.; Villalgordo, J. M. Tetrahedron 2001, 57, 4371-4388.
61. Synthesized according to: Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2003, 1, 1830-1832.
62. 3, MeOH) due to their dominating zwitterionic nature.
63. Izdebski, J.; Kunce, D. J. Pept. Sci. 1997, 3, 141-144.
64. Tartar, A.; Gesquiere, J. C. J. Org. Chem. 1979, 44, 5000-5001.
65. It was noticed that the cyclization experiments required the addition of DiPEA prior to the addition of the carbodiimide to obtain reproducible results.
66. This method has been developed by Van Leeuwen/Van der Made at Shell (Amsterdam).