Highly efficient template-based preparation of shape-persistent macrocyclics

Macromolecular Symposia

Volumn 142, Issue , 1999, Pages 185-191

  Hoger S ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033450571     PISSN: 10221360     EISSN: None     Source Type: Journal    
DOI: 10.1002/masy.19991420118     Document Type: Article

References (38)

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9. For macrocyclic host molecules based on the phenyl-ethynyl backbone see e.g. (a) H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1989, 1714; (b) L.G. Mackeay, H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 43; (c) H.L. Anderson, J.K.M Sanders, J. Chem. Soc. Chem. Commun. 1992, 946; (d) S.Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem., Int. Ed. Engl. 1995, 34, 1596; (e) D.L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313.
10. For macrocyclic host molecules based on the phenyl-ethynyl backbone see e.g. (a) H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1989, 1714; (b) L.G. Mackeay, H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 43; (c) H.L. Anderson, J.K.M Sanders, J. Chem. Soc. Chem. Commun. 1992, 946; (d) S.Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem., Int. Ed. Engl. 1995, 34, 1596; (e) D.L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313.
11. For macrocyclic host molecules based on the phenyl-ethynyl backbone see e.g. (a) H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1989, 1714; (b) L.G. Mackeay, H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 43; (c) H.L. Anderson, J.K.M Sanders, J. Chem. Soc. Chem. Commun. 1992, 946; (d) S.Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem., Int. Ed. Engl. 1995, 34, 1596; (e) D.L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313.
12. For macrocyclic host molecules based on the phenyl-ethynyl backbone see e.g. (a) H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1989, 1714; (b) L.G. Mackeay, H.L. Anderson, J.K.M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 43; (c) H.L. Anderson, J.K.M Sanders, J. Chem. Soc. Chem. Commun. 1992, 946; (d) S.Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem., Int. Ed. Engl. 1995, 34, 1596; (e) D.L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313.
13. (a) L.T. Scott, M.J. Cooney, D. Johnels, J. Am. Chem. Soc. 1990, 112, 4054;
14. (b) L.T. Scott, M.J. Cooney, in Modern Acetylene Chemistry (ed. P.J. Stang, F. Diederich), VCH, Weinheim, 1995, pp. 321.
15. For example, see for a comparison: (a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424 and (b) J. S. Moore, J. Zhang, Angew. Chem. Int. Ed. Engl. 1992, 31, 292, as well as (c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; and (d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
16. For example, see for a comparison: (a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424 and (b) J. S. Moore, J. Zhang, Angew. Chem. Int. Ed. Engl. 1992, 31, 292, as well as (c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; and (d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
17. For example, see for a comparison: (a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424 and (b) J. S. Moore, J. Zhang, Angew. Chem. Int. Ed. Engl. 1992, 31, 292, as well as (c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; and (d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
18. For example, see for a comparison: (a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424 and (b) J. S. Moore, J. Zhang, Angew. Chem. Int. Ed. Engl. 1992, 31, 292, as well as (c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; and (d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
19. (a) S. Höger, V. Enkelmann, Angew. Chem. Int. Ed. Engl. 1995, 34, 2713;
20. (b) S. Höger, A.-D. Meckenstock, S. Müller, Chem. Eur. J. 1998, 4, 2421.
21. S. Höger, A.-D. Meckenstock, H. Pellen, J. Org. Chem. 1997, 62, 4556.
22. (a) O. Mitsunobu, Synthesis 1981, 1;
23. (b) D.L. Hughes, Org. React. 1992, 42, 335.
24. For recent articles dealing with template reactions see e.g.: (a) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993. (b) S. Anderson, H.L. Anderson, J.K.M. Sanders, Acc Chem. Res. 1993, 26, 469; (c) R. Hoss, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1994, 33, 375; (d) J.L. Atwood, J.E.D. Davies, D.D. Macnicol, F. Vögtle, (ed.), Comprehensive Supramolecular Chemistry, vol. 9, Elsevier Science Ltd., Oxford, 1996.
25. For recent articles dealing with template reactions see e.g.: (a) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993. (b) S. Anderson, H.L. Anderson, J.K.M. Sanders, Acc Chem. Res. 1993, 26, 469; (c) R. Hoss, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1994, 33, 375; (d) J.L. Atwood, J.E.D. Davies, D.D. Macnicol, F. Vögtle, (ed.), Comprehensive Supramolecular Chemistry, vol. 9, Elsevier Science Ltd., Oxford, 1996.
26. For recent articles dealing with template reactions see e.g.: (a) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993. (b) S. Anderson, H.L. Anderson, J.K.M. Sanders, Acc Chem. Res. 1993, 26, 469; (c) R. Hoss, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1994, 33, 375; (d) J.L. Atwood, J.E.D. Davies, D.D. Macnicol, F. Vögtle, (ed.), Comprehensive Supramolecular Chemistry, vol. 9, Elsevier Science Ltd., Oxford, 1996.
27. For recent articles dealing with template reactions see e.g.: (a) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993. (b) S. Anderson, H.L. Anderson, J.K.M. Sanders, Acc Chem. Res. 1993, 26, 469; (c) R. Hoss, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1994, 33, 375; (d) J.L. Atwood, J.E.D. Davies, D.D. Macnicol, F. Vögtle, (ed.), Comprehensive Supramolecular Chemistry, vol. 9, Elsevier Science Ltd., Oxford, 1996.
28. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
29. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
30. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
31. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
32. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
33. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
34. For some reviews and examples on the use of covalently attached templates in organic synthesis see e.g.: (a) R. Breslow, Acc. Chem. Res. 1980, 13, 170; (b) K.S. Feldman, Y.B. Lee, J. Am. Chem. Soc., 1987, 109, 5850; (c) J.W. Gillard, R. Fortin, E.L. Grimm, M. Maillard, M. Tjepkema, M.A. Bernstein, R. Glaser, Tetrahedron Lett., 1991, 32, 1145; (d) J.-I. Hong, S.K. Namgoong, A. Bernardi, W.C. Still, J. Am. Chem. Soc., 1991, 113, 5111; (e) S. Valverde, A.M. Gómez, J.C. López, B. Herradón, Tetrahedron Lett. 1996, 37, 1105; (f) F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, M. Gross, J. Chem. Soc. Chem. Commun. 1996, 797; (g) H. Weizman, J. Libman, A. Shanzer, J. Am. Chem. Soc., 1998, 120, 2188.
35. S. Höger, A.-D. Meckenstock, Tetrahedron Lett. 1998, 39, 1735.
36. S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, in press.
37. For early reports of the concept of intraannular functional groups see e.g.: (a) E. Weber, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1974, 13, 149; (b) E. Weber, F. Vögtle, Chem. Ber. 1976, 109, 1803.
38. For early reports of the concept of intraannular functional groups see e.g.: (a) E. Weber, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1974, 13, 149; (b) E. Weber, F. Vögtle, Chem. Ber. 1976, 109, 1803.