Functionalized carbosilane dendritic species as soluble supports in organic synthesis

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6338-6344

  Hovestad, Neldes J ^a   Ford, Allan ^a   Jastrzebski, Johann T B H ^a   Van Koten, Gerard ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; BROMINE; CARBOXYLIC ACID; DENDRIMER; ESTER DERIVATIVE; HYDROGEN; IMINE; ORGANIC COMPOUND; REAGENT; SILANE DERIVATIVE; ZINC;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR WEIGHT; ORGANIC CHEMISTRY; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

LACTAMS; SILANES; SOLUBILITY;

EID: 0034613128     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991726k     Document Type: Article

References (48)

1. (a) Leznoff, C. C. Chem. Soc. Rev. 1974, 3, 65.
2. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
3. (c) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
4. (d) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
5. (e) Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153.
6. (f) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C Tetrahedron 1997, 53, 5643.
7. (g) Guillermo, A. M.; Corbett, J. W.; DeGrado, W. F. J. Org. Chem. 1998, 63, 1172-1177.
8. (h) Kearney, P. C.; Fernandez, M.; Flygare, J. A. J. Org. Chem. 1998, 63, 196-200.
9. (a) Geckeler, K.; Pillai, V. N. R.; Mutter, M. Adv. Polym. Sci. 1981, 39, 65.
10. (b) Braca, G.; Di Girolamo, M.; Raspolli Galletti, A. M.; Sbrana, G.; Brunelli, M.; Bertolini, G. J. Mol. Catal. 1992, 74, 421.
11. (c) Shah, J. N.; Ram, R. N. J. Mol. Catal. 1992, 77, 235.
12. (d) van de Kuil, L. A.; Grove, D. M.; Zwikker, J. W.; Jenneskens, W.; Drenth, W.; van Koten, G. Chem. Mater. 1994, 6, 1676.
13. (e) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053.
14. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
15. (a) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193.
16. (b) Fréchet, J. M. J. Science 1994, 263, 1710.
17. (c) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules-Concepts, Synthesis, Perspectives; VCH: Weinheim, 1996.
18. (d) Vögtle, F. Dendrimer Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998.
19. (e) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 884.
20. (f) Knapen, J. W, J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. W.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
21. (g) van Koten, G.; Jastrzebski, J. T. B. H. Polym. Mater. Sci. Eng. 1997, 77, 75.
22. (h) Hovestad, N. J.; Hoare, J. L.; Jastrzebski, J. T. B. H.; Canty, A. J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1999, 18, 2970.
23. (i) Wells, N. J.; Basso, A.; Bradley, M. Biopolymers 1998, 47, 381.
24. Kim, R. M.; Manna, M.; Hutchins, S. M.; Griffin, P. R.; Yates, N. A.; Bernick, A. M.; Chapman, K. T. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10012.
25. Hovestad, N. J.; Jastrzebski, J. T. B. H.; van Koten, G. Polym. Mater. Sci. Eng. 1999, 80, 53.
26. Hovestad, N. J.; Eggeling, E. B.; Heidbüchel, J. H.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 1655.
27. Van der Made, A. W.; van Leeuwen, P. W. M. N. J. Chem. Soc., Chem. Commun. 1992, 1400.
28. Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621.
29. (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171.
30. (b) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
31. (c) Fenger, I.; Le Drian, C. Tetrahedron Lett. 1998, 39, 4287.
32. (d) Wendeborn, S.; Berteina, S.; Brill, W. K.-D.; De Mesmaeker, A. Synlett 1998, 671.
33. (a) Jastrzebski, J. T. B. H.; van der Steen, F. H. van Koten, G. Recl. Trav. Chim. Pays-Bas, 1987, 106, 516.
34. (b) Jastrzebski, J. T. B. H.; van Koten, G. Bioorg. Med. Chem. Lett. 1993, 3, 2351.
35. (c) van Maanen, H. L.; Kleijn, H.; Jastrzebski, J. T. B. H.; Verweij, J.; Kieboom, A. P. G.; van Koten, G. J. Org. Chem. 1995, 60, 4331.
36. Recently, Ruhland et al. reported the solid-phase combinatorial synthesis of β-lactams via a [2 + 2] cycloaddition reaction of ketenes with resin-bound imines derived from amino acids. Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253.
37. (a) van der Steen F. H.; Boersma, J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1990, 390, C21.
38. (b) van der Steen, F. H.; Boersma, J.; Spek, A. L.; van Koten, G. Organometallics 1991, 10, 2468.
39. (c) Kleijn, H.; van Maanen, H. L.; Jastrzebski, J. T. B. H.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1992, 111, 497.
40. (d) van Maanen, H. L.; Kleijn, H.; Jastrzebski, J. T. B. H.; van Koten, G. Red. Trav. Chim. Pays-Bas 1994, 113, 567.
41. The excellent cis-trans selectivity was rationalized via a six-membered cyclic transition state, involving a (Z)-enolate and a (E)-imine, analogous to the transition state models for the related aldol reaction. See: Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Seebach, D. Angew. Chem. 1988, 100, 1685.
42. The excellent cis-trans selectivity was rationalized via a six- membered cyclic transition state, involving a (Z)-enolate and a (E)- imine, analogous to the transition state models for the related aldol reaction. See: Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Seebach, D. Angew. Chem. 1988, 100, 1685.
43. van der Steen, H.; Kleijn, H.; Britovsek, G. J.; Jastrzebski, J. T. B. H.; van Koten, G. J. Org. Chem. 1992, 57, 3906.
44. Dayagi, S.; Degani, Y. The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: London, 1970; p 61.
45. Hamilton, R. T.; Butler, J. A. J. Chem. Soc. 1932, 2283.
46. Brunner, J.; Richards, F. M. J. Biol. Chem. 1981, 225, 3319.
47. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446.
48. van Maanen, H. L.; Kleijn, H.; Jastrzebski, J. T. B. H.; van Koten G. Recl. Trav. Chim. Pays-Bas 1994, 113, 567.