SN1-like reactions of bicyclic α-amino ethers with sulfur, nitrogen, and carbon nucleophiles. Synthesis of 1-azabicyclo[3.2.2]nonanes functionalized at carbon C2 and C6 with complete stereocontrol

Organic Letters

Volumn 4, Issue 19, 2002, Pages 3179-3182

  Röper, Stefanie ^a   Wartchow, Rudolf ^a   Hoffmann, H Martin R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN; SULFUR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZA COMPOUNDS; CARBON; ETHERS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM; SULFUR;

EID: 0037136469     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026342m     Document Type: Article

References (36)

1. For examples, see: (a) Nomofungin: Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2001, 66, 8717.
2. (b) Communesins, Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355.
3. (a) Ruggles, C. J.; Halpern, A. M. J. Am. Chem. Soc. 1988, 110, 5692.
4. (b) Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W.-K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183.
5. (c) Vorob'eva, V. Ya.; Mikhlina, E. E.; Turchin, K. F. Yakhontov, L. N. Khim. Geterotsikl. Soedin. 1970, 8, 1037.
6. (d) Yanina, A. D.; Mikhlina, E. E.; Rubtsov, M. V. Zh. Org. Khim. 1966, 2, 1707.
7. (e) Prelog, V.; Cerkovnikov, E. Liebigs. Ann. 1937, 532, 83.
8. (a) Lowe, J. A., III. PCT Int. Appl. WO 9215585, 1992.
9. (b) Lowe, J. A., III; Drozda, S. E.; Snider, R. M.; Longo, K. P.; Rizzi, J. P. Bioorg. Med. Chem. Lett. 1993, 3, 921.
10. (c) King, F. D.; Joiner, K. A. Eur. Pat. App. EP 214772, 1987 (US 4798829, 1986).
11. Mueller, R. A.; Partis, K. A.; Deason, J. R. Eur. Pat. Appl. EP 190684, 1986.
12. Hoffmann, H. M. R.; Plessner, T.; von Riesen, C. Synlett 1996, 690 and subsequent papers.
13. Röper, S.; Frackenpohl, J.; Schrake, O.; Wartchow, R.; Hoffmann, H. M. R. Org. Lett. 2000, 2, 1661.
14. For general aspects of preparative carbocation chemistry, see: (a) Yoshida, T., Suga, S. Chem. Eur. J. 2002, 8, 2651-2558.
15. (b) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1393; Angew. Chem. 1995, 107, 1519 (Nobel lecture).
16. (b) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1393; Angew. Chem. 1995, 107, 1519 (Nobel lecture).
17. (c) Methoden der Organischen Chemie, HoubenWeyl; Hanack, M., Ed.; Thieme: Stuttgart, 1990; Vol. E19c.
18. (d) Denmark, S. E.; Willson, T. M. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed.; Kluwer Academic: Dordrecht, 1989; pp 247-263.
19. (a) Hiemstra, H.; Fortgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1984, 25, 3115. For a review on additions to N-acyliminium ions, see:
20. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. See also:
21. (c) Schroth, W.; Jahn, U. J. Prakt. Chem. 1998, 340, 287-299.
22. For a review on α-amino nitriles, see: (a) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359-373 and references therein.
23. (b) Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. 1998, 1, 63.
24. (c) Suginome, M.; Yamamoto, A.; Ito, Y. J. Chem. Soc., Chem. Commun. 2002, 1392
25. Replacement of the vinyl group by hydrogen generates enantiomers. The term pseudo-enantiomer is used routinely for related pairs of Cinchona alkaloids, e.g., quinine and quinidine.
26. Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868.
27. (a) Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501.
28. (b) Yamamoto, Y.; Schmid, M. J. Chem. Soc., Chem. Commun. 1989, 1310.
29. Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1988, 29, 367;
30. a 11.2) for desilylation of ketene acetal in situ.
31. 4, evaporated, and purified by column chromatography (PE/MTBE 1:1) to furnish 1-ester (66%, 70 mg).
32. Work up with KF/water increased the yield from 39 to 70%.
33. Cambridge Crystallographic Data Centre CCDC 185368. The X-ray structure was plotted by Molekel 4.1. Flükiger, H. P.; Lüthi, H. P.; Portmann, S.; Weber, J. Swiss Center for Scientific Computing; Manno: Switzerland, 2000-2001.
34. For a leading reference on iminium ions, see: Mayr, H.; Ofial, A. R.; Sauer, J.; Schmied, B. Eur. J. Org. Chem. 2000, 2013.
35. E and Z isomers of [3.2.1]bicyclic imines with nitrogen in the nonbridgehead position: (a) Sheridan, R. S.; Ganzer, G. A. J. Am. Chem. Soc. 1983, 105, 6158.
36. (b) Radziszewski, J. G.; Downing, J. W.; Wentrup, C.; Kaszynski, P.; Jawdosiuk, M.; Michl. J. J. Am. Chem. Soc. 1985, 107, 2799.