Conformational Preference and Configurational Control of Highly Symmetric Spirobi[dibenzazepinium] Cation

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3939-3942

  Vial, Laurent ^a   Lacour, Jérôme ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

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ARTICLE;

EID: 0012131697     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026800r     Document Type: Article

References (49)

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3. Dolling, U. H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447. Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934. Zhang, F.; Corey, E. J. Org. Lett. 2001, 3, 639-641. Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 6447-6453. Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J. C.; Cahard, D. Synthesis 2001, 1742-1746.
4. Dolling, U. H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447. Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934. Zhang, F.; Corey, E. J. Org. Lett. 2001, 3, 639-641. Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 6447-6453. Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J. C.; Cahard, D. Synthesis 2001, 1742-1746.
5. Dolling, U. H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447. Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931-1934. Zhang, F.; Corey, E. J. Org. Lett. 2001, 3, 639-641. Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 6447-6453. Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J. C.; Cahard, D. Synthesis 2001, 1742-1746.
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21. See also: (c) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451-454. (d) Rashidi-Ranjbar, P.; Taghvaei-Ganjali, S.; Wang, S. L.; Liao, F. L.; Heydari, A. J. Chem. Soc., Perkin Trans. 2 2001, 1255-1260. (e) Kiupel, B.; Niederalt, C.; Nieger, M.; Grimme, S.; Vögtle, F. Angew. Chem., Int. Ed. 1998, 37, 3031-3034. (f) Sutherland, I. O.; Ramsay, M. V. J. Tetrahedron 1965, 21, 3401-3408.
22. See also: (c) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451-454. (d) Rashidi-Ranjbar, P.; Taghvaei-Ganjali, S.; Wang, S. L.; Liao, F. L.; Heydari, A. J. Chem. Soc., Perkin Trans. 2 2001, 1255-1260. (e) Kiupel, B.; Niederalt, C.; Nieger, M.; Grimme, S.; Vögtle, F. Angew. Chem., Int. Ed. 1998, 37, 3031-3034. (f) Sutherland, I. O.; Ramsay, M. V. J. Tetrahedron 1965, 21, 3401-3408.
23. See also: (c) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451-454. (d) Rashidi-Ranjbar, P.; Taghvaei-Ganjali, S.; Wang, S. L.; Liao, F. L.; Heydari, A. J. Chem. Soc., Perkin Trans. 2 2001, 1255-1260. (e) Kiupel, B.; Niederalt, C.; Nieger, M.; Grimme, S.; Vögtle, F. Angew. Chem., Int. Ed. 1998, 37, 3031-3034. (f) Sutherland, I. O.; Ramsay, M. V. J. Tetrahedron 1965, 21, 3401-3408.
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33. NMR desymmetrization of meso derivatives can occur upon the addition of external chiral shift agents. See: Reetz, M. T. Pure Appl. Chem. 1996, 68, 1279-1283. Huskens, J.; Reetz, M. T. Eur. J. Org. Chem. 1999, 1775-1786. Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313-3361. Reetz, M. T.; Rudolph, J.; Mynott, R. J. Am. Chem. Soc. 1996, 118, 4494-4495.
34. NMR desymmetrization of meso derivatives can occur upon the addition of external chiral shift agents. See: Reetz, M. T. Pure Appl. Chem. 1996, 68, 1279-1283. Huskens, J.; Reetz, M. T. Eur. J. Org. Chem. 1999, 1775-1786. Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313-3361. Reetz, M. T.; Rudolph, J.; Mynott, R. J. Am. Chem. Soc. 1996, 118, 4494-4495.
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40. This is rather improbable considering the results of Maruoka et al. See ref 4.
41. -1.
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