The first cyclodiasteromeric [3]rotaxane

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3528-3530

  Schmieder, Roland ^a   Hübner, Gosia ^a   Seel, Christian ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Chirality; Cycloenantiomerism; Mechanical bonding; Rotaxanes; Supramolecular chemistry

Indexed keywords

TARTARIC ACID;

ARTICLE; CHEMICAL BINDING; CHIRALITY; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345008880     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3528::AID-ANIE3528>3.0.CO;2-N     Document Type: Article

References (55)

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2. a) Molecular Catenanes, Rotaxanes and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999;
3. b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908;
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5. c) D. K. Mitchell, J.-P. Sauvage, Angew. Chem. 1988, 100, 985-987; Angew. Chem. Int. Ed. Engl. 1988, 27, 930-932;
6. d) J.-F. Nierengarten, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 375-376;
7. for the enantiomeric resolution, see e) Y. Kaida, Y. Okamoto, J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, Tetrahedron Lett. 1993, 34, 1019-1022.
8. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
9. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
10. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
11. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
12. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
13. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
14. For topologically chiral catenanes, see a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511; b) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064; c) J.-C. Chambrom, C. O. Dietrich- Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 132-159; d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212; e) C.-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660; f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T. J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine Press, New York, 1996, p. 319.
15. G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, pp. 11-15.
16. Chiral pseudorotaxanes: a) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986; b) M. Asakawa, P. R. Ashton, W. Hayes, H. M. Janssen, E. W. Meijer, S. Menzer, D. Pasini, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 920-931.
17. Chiral pseudorotaxanes: a) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986; b) M. Asakawa, P. R. Ashton, W. Hayes, H. M. Janssen, E. W. Meijer, S. Menzer, D. Pasini, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 920-931.
18. Chiral [2]rotaxanes: a) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. 1997, 495-499; b) P. R. Ashton, S. R. L. Everitt, M.Gómez-López, N. Jayamaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694; c) T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007: d) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908; e) first cycloenantiomeric [2]rotaxane: C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
19. Chiral [2]rotaxanes: a) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. 1997, 495-499; b) P. R. Ashton, S. R. L. Everitt, M.Gómez-López, N. Jayamaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694; c) T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007: d) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908; e) first cycloenantiomeric [2]rotaxane: C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
20. Chiral [2]rotaxanes: a) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. 1997, 495-499; b) P. R. Ashton, S. R. L. Everitt, M.Gómez-López, N. Jayamaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694; c) T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007: d) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908; e) first cycloenantiomeric [2]rotaxane: C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
21. Chiral [2]rotaxanes: a) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. 1997, 495-499; b) P. R. Ashton, S. R. L. Everitt, M.Gómez-López, N. Jayamaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694; c) T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007: d) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908; e) first cycloenantiomeric [2]rotaxane: C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
22. Chiral [2]rotaxanes: a) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. 1997, 495-499; b) P. R. Ashton, S. R. L. Everitt, M.Gómez-López, N. Jayamaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694; c) T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007: d) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908; e) first cycloenantiomeric [2]rotaxane: C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
23. a) N. Solladié, J.-C. Chambron, J.-P. Sauvage, J. Am. Chem. Soc. 1999, 121, 3684-3692;
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26. c) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959;
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28. e) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310;
29. f) P. R. Ashton, P. T. Glink, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 729-736;
30. g) D. B. Amablino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020;
31. h) N. Solladié. J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Int. Ed. Engl. 1996, 35, 906-909;
32. h) N. Solladié. J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Int. Ed. Engl. 1996, 35, 906-909;
33. i) P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradský, M. T. Gandolfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951;
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35. k) D. B. Amabilino, P. R. Ashton, M. Belohradský, F. M. Raymo, J. F. Stoddart, J. Chem Soc. Chem. Commun. 1995, 747-750.
36. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
37. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
38. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
39. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
40. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
41. The terms cycloenantiomerism and cyclodiastereomerism were introduced by Prelog et al., and the phenomena were realized in cyclopeptides. This stereoisomerism occurs in cyclic arrangements of several centrally chiral elements in combination with an orientation of the macrocycle: a) V. Prelog, H. Gerlach. Helv. Chim. Acta 1964, 47, 2288-2294; b) H. Gerlach, J. A. Owtschinnikow, V. Prelog, Helv. Chim. Acta 1964, 47, 2294-2302; c) E. L. Eliel, Stereochemie der Kohlenstoffverbindungen, Verlag Chemie, Weinheim, 1966; d) E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds. of German version: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998; e) M. Chorev, M. Goodman, Acc. Chem. Res. 1992, 25, 266-272; f) K. Mislow, Chimia 1986, 40, 395-402.
42. a) G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398; Angew. Chem. Int. Ed. 1999, 38, 383-386;
43. a) G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398; Angew. Chem. Int. Ed. 1999, 38, 383-386;
44. b) C. Seel, F. Vögtle, Chem. Eur. J. 2000, in press;
45. c) C. Reuter, W. Wienard, G. M. Hübner, C. Seel, F. Vögtle, Chem. Eur. J. 1999, 5, 2692-2697.
46. 2: C 73.06, H 6.69, N 4.12, S 1.88; found: C 72.98, H 6.77, N 4.13, S 2.31; the dichloromethane is detected by NMR spectroscopy.
47. a) E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289;
48. b) Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043;
49. b) Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043;
50. c) for polarimetric detection during liquid chromatography, see A. Mannschreck, N. Pustet, F. Brandl, GIT Spezial 1999, 1, 34-36.
51. 1 in chloroform/n-hexane (1/1).
52. 3); circular dichroism spectra: JASCO Spectropolarimeter J-720, cell 0.1 mm (trifluoroethanol).
53. S. Grimme, J. Harren, A. Sobanski, F. Vögtle, Eur. J. Org. Chem. 1998, 1499-1509.
54. a)D. A. Leigh, A. Murphy, Chem. Int. 1999, 3, 178;
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