Synthesis and conformational study of water-soluble, rigid, rodlike oligopiperidines

Angewandte Chemie - International Edition

Volumn 45, Issue 4, 2006, Pages 588-591

  Semetey, Vincent ^a   Moustakas, Demetri ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Molecular dynamics; Molecular rods; NMR spectroscopy; Oligomers; Structure elucidation

Indexed keywords

MOLECULAR RODS; PIPERIDINE; RODLIKE STRUCTURES; STRUCTURE ELUCIDATION;

CONFORMATIONS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID STATE DEVICE STRUCTURES; STRUCTURAL ANALYSIS; SYNTHESIS (CHEMICAL);

OLIGOMERS;

PIPERIDINE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SOLUBILITY; SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; SOLUBILITY; TEMPERATURE; WATER;

EID: 31044455454     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502991     Document Type: Article

References (21)

1. a) P. F. H. Schwab, M. D. Levin, J. Michl, Chem. Rev. 1999, 99, 1863 - 1933;
2. b) J. S. Moore, Acc. Chem. Res. 1997, 30, 402 - 413;
3. c) J. M. Tour, Acc. Chem. Res. 2000, 33, 791 - 804.
4. a) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173 - 180;
5. b) R. P. Cheng, S. H. Gellmann, W. F. DeGrado, Chem. Rev. 2001, 101, 3219 - 3232;
6. c) D. J. Hill, J. M. Matthiew, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893 - 4011.
7. N. Sakai, J. Mareda, S. Matile, Acc. Chem. Res. 2005, 38, 79 - 87.
8. a) N. Aratani, H. S. Cho, T. K. Ahn, S. Cho, D. Kim, H. Sumi, A. Osuka J. Am. Chem. Soc., 2003, 125, 9668 - 9681;
9. b) C. Xu, A. Wakamiya, S. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 1638 - 1639.
10. a) L. Stryer, R. P. Haugland, Proc. Natl. Acad. Sci. USA 1967, 58, 719 - 726;
11. b) B. Schuler, E. A. Lipman, P. J. Steinbach, M. Kumke, W. A. Eaton, Proc. Natl. Acad. Sci. USA 2005, 102, 2754 - 2759.
12. a) P. S. Arora, A. Z. Ansari, T. P. Best, M. Ptashne, P. Dervan, J. Am. Chem. Soc. 2002, 124, 13 067 - 13 071;
13. b) H. Ungar-Waron, D. Gurari, E. Hurwitz, M. Sela, Eur. J. Immunol. 1973, 4, 201 - 205.
14. C. G. Levins, C. E. Schafmeister, J. Am. Chem. Soc. 2003, 125, 4702 - 4703.
15. R. J. Willemse, J. J. Piet, J. M. Warman, F. Hartl, J. W. Verhoeven, A. M. Brouwer, J. Am. Chem. Soc. 2000, 122, 3721 - 3730.
16. A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849 - 3862.
17. a) F. W. Vierhapper, E. L. Eliel, J. Org. Chem. 1979, 44, 1081 - 1087;
18. b) E. L. Eliel, F. W. Vierhapper, J. Am. Chem. Soc. 1975, 97, 2424 - 2430;
19. c) E. L. Eliel, F. W. Vierhapper, J. Am. Chem. Soc. 1974, 96, 2257 - 2259.
20. C. Jaime; E. J. Ōsawa, J. Chem. Soc. Chem. Commun. 1983, 12, 708 - 709.
21. 2 = 0.1729 (I > 2σ(I)). CCDC 263974 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.