Conformational analysis of (R,S)-4-amido-2,4-dimethyl-butyric acid derivatives

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 5983-5986

  Hoffmann, Reinhard W ^a   Lazaro, Miguel A ^a   Caturla, Francisco ^a   Framery, Eric ^a   Valancogne, Ingrid ^b   Montalbetti, Christian A G N ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Conformation; Hydrocarbon backbone

Indexed keywords

4 AMIDO 2,4 DIMETHYLBUTYRIC ACID; BUTYRIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033551675     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01226-5     Document Type: Article

References (31)

1. a) U. Koert Angew. Chem. 109, 1922 (1997); Angew. Chem. Int. Ed. Engl. 36, 1836 (1997);
2. a) U. Koert Angew. Chem. 109, 1922 (1997); Angew. Chem. Int. Ed. Engl. 36, 1836 (1997);
3. b) D. Seebach and J. L. Matthews J. Chem. Soc., Chem. Commun., 2015 (1997);
4. c) D. Seebach, K. Gademann, J. V. Schreiber, J. L. Matthews, T. Hintermann, B. Jaun, L. Oberer, U. Hommel and H. Widner Helv. Chim. Acta 80, 2033 (1997);
5. d) S. H. Gellman Accts. Chem. Res. 31, 173 (1998);
6. e) Y.-D. Wu and D.-P. Wang J. Am. Chem. Soc. 120, 13485 (1998);
7. f) X. Daura, K. Gademann, B. Jaun, D. Seebach, W. F. Van Gunsteren and A. E. Mark Angew. Chem. 111, 249 (1999); Angew. Chem. Int. Ed. Engl. 38, 236 (1999);
8. f) X. Daura, K. Gademann, B. Jaun, D. Seebach, W. F. van Gunsteren and A. E. Mark Angew. Chem. 111, 249 (1999); Angew. Chem. Int. Ed. Engl. 38, 236 (1999);
9. g) K. Gademann, B. Jaun, D. Seebach, R. Perozzo, L. Scapozzo and G. Folkers Helv. Chim. Acta 82, 1 (1999);
10. h) D. H. Appella, J. J. Barchi Jr., S. R. Durell and S. H. Gellman J. Am. Chem. Soc. 121, 2309 (1999);
11. i) B. W. Gung, D. Zou, A. M. Stalcup and C. E. Cottrell J. Org. Chem. 64, 2176 (1999).
12. a) T. Hintermann, K. Gademann, B. Jaun and D. Seebach Helv. Chim. Acta 81, 983 (1998);
13. b) S. Hanessian, X. Luo, R. Schaum and S. Michnick J. Am. Chem. Soc. 120, 8569 (1998).
14. Y. Kalo, N. Fusetani, S. Matsunaga, K. Hashimoto and K. Koseki J. Org. Chem. 53, 3930 (1988).
15. a) T. Owa, A. Haupt, M. Otsuka, S. Kobayashi, N. Tomioka, A. Itai, M. Ohno, T. Shiraki, M. Uesugi, Y. Sugiura and K. Maeda Tetrahedron 48, 1193 (1992);
16. b) D. L. Boger and H. Cai Angew. Chem. 111, 470 (1999); Angew. Chem. Int. Ed. Engl. 38, 448 (1999).
17. b) D. L. Boger and H. Cai Angew. Chem. 111, 470 (1999); Angew. Chem. Int. Ed. Engl. 38, 448 (1999).
18. D. L. Boger, T. M. Ramsey, H. Cai, S. T. Hoehn and J. Stubbe J. Am. Chem. Soc. 120, 9149 (1998).
19. S. M. Lui, D. E. Vanderwall, W. Wu, X.-J. Tang, C. J. Turner, J. W. Kozarich and J. Stubbe J. Am. Chem. Soc. 119, 9603 (1997).
20. P. M. Pihko and A. M. P. Koskinen J. Org. Chem. 63, 92 (1998).
21. a) R. W. Hoffmann Angew. Chem. 104, 1147 (1992); Angew. Chem. Int. Ed. Engl. 31, 1124 (1992);
22. a) R. W. Hoffmann Angew. Chem. 104, 1147 (1992); Angew. Chem. Int. Ed. Engl. 31, 1124 (1992);
23. b) R. W. Hoffmann, M. Stahl, U. Schopfer and G. Frenking Chem. Eur. J. 4, 559 (1998).
24. 14 in the presence of alcohols led us to the various N-acylated derivatives 8-10 and 13 listed in the table.
25. The amides 11 and 12 were prepared by attaching the amido acid 10 to 2-chlorotrityl resin and coupling with the second amino acid by standard methods using O-benzotriazolyl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) as coupling reagent.
26. A. M. P. Koskinen and P. M. Pihko Tetrahedron Lett. 35, 7417 (1994).
27. M. F. Semmelhack, R. D. Stauffer and A. Yamashita J. Org. Chem. 42, 3180 (1977).
28. For leading references see: P. J. Kocienski, R. C. D. Brown, A. Pommier, M. Procter and B. Schmidt J. Chem. Soc., Perkin Trans, 1, 9 (1998).
29. a) R. W. Hoffmann, H.-J. Zeiß, W. Ladner and S. Tabche Chem. Ber. 115, 2357 (1982);
30. b) M. Sefkow, A. Neidlein, T. Sommerfeld, F. Sternfeld, M. A, Maestro and D. Seebach Liebigs Ann. Chem., 719 (1994).
31. K. Ninomiya, T. Shioiri and S. Yamada Tetrahedron 30, 2151 (1974).