Tripodal synthetic peptide bundles

Chemistry - A European Journal

Volumn 3, Issue 8, 1997, Pages 1254-1268

  Trojandt, Gunter ^a   Herr, Ulrike ^a   Polborn, Kurt ^a   Steglich, Wolfgang ^a  

^a Inst für Physikalische Chemie   (Germany)

Author keywords

Peptide bundles; Peptides; Pseudo peptides; Template synthesis; Tripodal Ligands

Indexed keywords

EID: 0030880229     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030813     Document Type: Article

References (76)

1. a) R. Breslow, Acc. Chem. Res. 1995, 28, 146-153;
2. b) R. Breslow, ibid. 1980, 13, 170-177.
3. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
4. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
5. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
6. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
7. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
8. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
9. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
10. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
11. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
12. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
13. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
14. Some recent examples are given by a) D. J. Cram, Science 1988, 240, 760-767; b) S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275-284; c) J. Wolfe, A. Muehldorf, J. Rebek, J. Am. Chem. Soc. 1991, 113, 1453-1454; d) V. J. Jubian, A. Veronese, R. P. Dixon, A. D. Hamilton, Angew. Chem. Int. Ed. Engl. 1995, 34, 1237-1239; e) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511; f) M. R. Ghadiri, M. A. Case, Angew. Chem. Int. Ed. Engl. 1993, 32, 1594-1597; g) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33-55; h) H.-J. Schneider, Angew. Chem. Int. Ed. 1993, 32, 848-850; i) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395; j) F. Diederich, H.-D. Lutter, J. Am. Chem. Soc. 1989, 111, 8438-8446; k) N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241-9284; l) M. Goodman, G. Melacini, Y. Feng, J. Am. Chem. Soc. 1996, 118, 10928-10929.
15. a) M. R. Carrasco, W. C. Still, Chem. Biol. 1995, 2, 205-212.
16. a) J. R. Granja, M. R. Ghadiri, J. Am. Chem. Soc. 1994, 116, 10785-10786;
17. b) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304.
18. a) L. Zelikovich, J. Libman, A. Shanzer, Nature 1995, 374, 790-792;
19. b) E. C. Constable, ibid. 1995, 374, 760-761.
20. a) Y. Tor, J. Libman, A. Shanzer, C. E. Felder, S. Lifson, J. Am. Chem. Soc. 1992, 114, 6653-6661;
21. b) Y. Tor, J. Libman, A. Shanzer, C. E. Felder, S. Lifson, ibid. 1992, 114, 6661-6671;
22. c) I. Dayan, J. Libman, Y. Agi, A. Shanzer, Inorg. Chem. 1993, 32, 1467-1475.
23. H.-B. Kraatz, Angew. Chem. Int. Ed. Engl. 1994, 33, 2055-2056, and references therein.
24. a) K. N. Raymond, G. Müller, B. F. Matzanke, Top. Curr. Chem. 1984, 123, 49-102;
25. b) J. Ohkanda, A. Katoh, J. Org. Chem. 1995, 60, 1583-1589;
26. c) E. J. Enemark, T. D. P. Stack, Angew. Chem. Int. Ed. Engl. 1995, 34, 996-998;
27. d) F. E. Hahn, W. W. Seidel, ibid. 1995, 34, 2700-2703;
28. e) G. Vériot, J.-P. Dutasta, G. Matouzenko, A. Collet, Tetrahedron 1995, 51, 389-400.
29. G. Trojandt, K. Polborn, W. Steglich, M. Schmidt, H. Nöth, Tetrahedron Lett. 1995, 36, 857-860.
30. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. Int. Ed. Engl. 1995, 34, 1449-1451.
31. R. Kober, W. Steglich, Liebigs Ann. Chem. 1983, 599-609.
32. For the use of templates in the synthesis of compounds with multiple peptide chains see: a) M. Mutter, G. G. Tuchscherer, C. Miller, K.-H. Altman, R. I. Carey, D. F. Wyss, A. M. Labhardt, J. E. Rivier, J. Am. Chem. Soc. 1992, 114, 1463-1470; b) G. Tuchscherer, Tetrahedron Lett. 1993, 34, 8419-8422.
33. For the use of templates in the synthesis of compounds with multiple peptide chains see: a) M. Mutter, G. G. Tuchscherer, C. Miller, K.-H. Altman, R. I. Carey, D. F. Wyss, A. M. Labhardt, J. E. Rivier, J. Am. Chem. Soc. 1992, 114, 1463-1470; b) G. Tuchscherer, Tetrahedron Lett. 1993, 34, 8419-8422.
34. C. Paulitz, 1995, unpublished results.
35. E. J. Corey, I. Székely, C. S. Shiner, Tetrahedron Lett. 1977, 40, 3529-3532.
36. Analytical HPLC was carried out on a Merck-Hitachi L-6200 intelligent pump equipped with a L-3000 photo diode detector with a silicagel column (Dr. Herbert Knaur KG, serial no. 8411261, Lichrosorb 5.607); eluent, 2-propanol:hexane 1:20. The two isomers 2a and 2b were eluted at 8.7 and 13.9 min, respectively.
37. C. J. Easton, S. C. Peters, Aust. J. Chem. 1990, 43, 87-97.
38. a) W. König, R. Geiger, Chem. Ber. 1970, 103, 788-798;
39. b) J. C. Sheehan, S. L. Ledis, J. Am. Chem. Soc. 1973, 95, 875-879.
40. Further examples for conglomerates: a) R. Krämer, J.-M. Lehn, A. DeCian, F. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 703-706; b) A. Streitwieser, C. H. Heathcock, Organische Chemie, VCH, Weinheim, 1986.
41. Further examples for conglomerates: a) R. Krämer, J.-M. Lehn, A. DeCian, F. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 703-706; b) A. Streitwieser, C. H. Heathcock, Organische Chemie, VCH, Weinheim, 1986.
42. a) N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Vally, California, 1983, 333;
43. b) N. Harada, K. Nakanishi, J. Am. Chem. Soc. 1969, 91, 3989-3991;
44. c) K. Nakanishi, N. Berova, R. W. Woody, Circular Dichroism -Principles and Applications, VCH, Weinheim, 1994;
45. d) Application of CD to the assignment of the screw sense of helical N-p-bromobenzoyl peptides: C. Toniolo, F. Formaggio, M. Crisma, H. E. Schoemaker, J. Kamphuis, Tetrahedron: Asymmetry 1994, 5, 507-510.
46. -3 [39].
47. -3 [39].
48. a) H. Kessler, Angew. Chem. Int. Ed. Eng. 1992, 21, 512-523;
49. b) J. S. Nowick, E. M. Smith, G. Noronha, J. Org Chem. 1995, 60, 7386-7387;
50. c) Y. A. Ovchinnikov, V. T. Ivanov, Tetrahedron 1975, 31, 2177-2209;
51. d) L. G. Pease, C. H. Niu, G. Zimmermann, J. Am. Chem. Soc. 1979, 101, 184-191;
52. e) Y. A. Bara, A. Friedrich, H. Kessler, M. Molter, Chem. Ber. 1978, 111, 1045-1057.
53. -3 [39].
54. W. H. Rastetter, T. J. Erickson, M. C. Venuzi, J. Org. Chem. 1981, 46, 3579-3590.
55. a) T. W. Greene, Protecting Groups in Organic Synthesis, Wiley, New York. 1981;
56. b) P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994;
57. c) G. L. Stahl, R. Walter, C. W. Smith, J. Org. Chem. 1978, 43, 2285-2286.
58. a) B. L. Vallee, D. S. Auld, Acc. Chem. Res. 1993, 26, 543-551;
59. b) C. A. Lesburg, D. W. Christianson, J. Am. Chem. Soc. 1995, 117, 6838-6844;
60. c) A. Looney, G. Parkin, R. Alsfasser, M. Ruf, H. Vahrenkamp, Angew. Chem. Int. Ed. Engl. 1992, 31, 92-93.
61. a) B. Monzyk, A. L. Crumbliss, J. Am. Chem. Soc. 1979, 101, 6203-6213;
62. b) S. J. Barclay, B. H. Huynh, K. N. Raymond, Inorg. Chem. 1984, 23, 2011-2018.
63. B. Hyrup, M. Egholm, P. E. Nielsen, P. Wittung, B. Nordén, O. Buchardt, J. Am. Chem. Soc. 1994, 116, 7964-7970.
64. S. Tomàs, M. C. Rotger, J. F. González, P. M. Deyà, P. Ballester, A. Costa, Tetrahedron Lett. 1995, 36, 2523-2526.
65. a) B. Schmidt, D. Seebach, Angew. Chem. Int. Ed. Engl. 1991, 30, 99-101;
66. b) B. Schmidt, D. Seebach ibid. 1991, 30, 1321-1323.
67. H. Lütjens, P. Knochel, Tetrahedron: Asymmetry 1994, 5, 1161-1162.
68. a) J. R. Luly, J. F. Dellaria, J. J. Plattner, J. L. Soderquist, N. Yi, J. Org. Chem. 1987, 52, 1487-1492;
69. b) Y. Hamada, T. Shioiri, Tetrahedron Lett. 1982, 23, 1193-1196.
70. -3 [39].
71. 3-THF solution was diluted with 10 mL water and titrated with a 1 N HCl standard solution against methyl orange.
72. 1H NMR spectrum only the crystalline (SSS) isomer is described.
73. 1H NMR spectrum only the crystalline (RRR) isomer is described.
74. M. Jäger, PhD thesis, University of Munich 1995.
75. [25a]
76. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100018. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).