Tetraaddition of PhLi to a ketocalixarene derivative

Organic Letters

Volumn 9, Issue 8, 2007, Pages 1577-1580

  Kuno, Lev ^a   Seri, Noa ^a   Biali, Silvio E ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

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EID: 34247528591     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070429w     Document Type: Article

References (42)

1. For reviews on calixarenes, see: (a) Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
2. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. (c) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
4. (d) Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon Press: Oxford, UK, 1996; Vol. 2, p 103.
5. (e) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
6. (f) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001.
7. (g) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, 2003; Chapter 19.
8. (a) Gutsche, C. D.; Iqbal, M. Org. Synth. 1989, 68, 234.
9. (b) Gutsche, C. D.; Dhawan, B.; Leonis, M.; Stewart. D. Org. Svnth. 1989, 68, 238.
10. (c) Munch, J. H.; Gutsche, C. D. Org. Synth. 1989, 68, 243.
11. For a review on resorcinarenes, see: Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
12. Fragment condensation method: (a) Tabatai, M.; Vogt, W.; Böhmer, V. Tetrahedron Lett. 1990, 31, 3295.
13. (b) Sartori, G.; Maggi, R.; Bigi, F.; Arduini, A.; Pastorio, A.; Porta, C. J. Chem. Soc., Perkin Trans. 1 1994, 1657.
14. (c) Sartori, G.; Bigi, F.; Porta, C.; Maggi, R.; Mora, R. Tetrahedron Lett. 1995, 36, 2311.
15. (d) Biali, S. E.; Böhmer, V.; Cohen, S.; Ferguson, G.; Grüttner, C.; Grynszpan, F.; Paulus, E. F.; Thondorf, I.; Vogt, W. J. Am. Chem. Soc. 1996, 118, 12938.
16. (e) Bergamaschi, M.; Bigi, F.; Lanfranchi, M.; Maggi, R.; Pastorio, A.; Pellinghelli, M. A.; Peri, F.; Porta, C.; Sartori, G. Tetrahedron 1997, 53, 13037.
17. (f) Tsue, H.; Enyo, K.; Hirao, K. Org. Lett. 2000, 2, 3071.
18. For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods, see: Böhmer, V. Liebigs Ann./ Recueil 1997, 2019.
19. Spirodienone route: (a) Agbaria, K.; Biali, S. E. J. Am. Chem. Soc. 2001, 123, 12495.
20. (b) Simaan, S.; Agbaria, K.; Biali, S. E. J. Org. Chem. 2002, 67, 6136.
21. (c) Simaan, S.; Biali, S. E. J. Org. Chem. 2003, 68, 3634.
22. (d) Simaan, S.; Biali, S. E. J. Org. Chem. 2003, 68, 7685.
23. For a review on Spirodienone calixarene derivatives, see: Biali, S. E. Synlett 2003, 1.
24. Homologous anionic ortho-Fries rearrangement: Middel, O.; Greff, Z.; Taylor, N. J.; Verboom, W.; Reinhoudt. D. N.; Snieckus, V. J. Org. Chem. 2000, 65, 667.
25. Alkylation of monolithiated tetramethoxy p-tert-butylcalix[4]arene: Scully, P. A.; Hamilton, T. M.; Bennett, J. L. Org. Lett. 2001, 3, 2741.
26. Görmar, G.; Seiffarth, K.: Schultz, M.; Zimmerman, J.; Flämig, G. Macromol. Chem. 1990, 191, 81.
27. See also: Seri, N.; Simaan, S.; Botoshansky, M.; Kaftory, M.; Biali, S. E. J. Org. Chem. 2003, 68, 7140.
28. Klenke, B.; Näther, C.; Friedrichsen, W. Tetrahedron Lett. 1998, 39, 8967.
29. Kumar, S.; Chawla, H. M.; Varadarajan, R. Tetrahedron Lett. 2002, 43, 7073.
30. Ref 1e, page 130.
31. Seri, N.; Biali, S. E. J. Org. Chem. 2005, 70, 5278.
32. The four isomers are analogous to the four forms of a resorcinarene of general formula 2 (R = alkyl or aryl). It should be stressed that these forms are configurational isomers and not conformers because their mutual interconversion requires cleavage of bonds.
33. The nomenclature is identical to the one used by Böhmer for the designation of the stereoisomers of resorcinarenes. One substituent on a bridge is taken as the reference (r). The arrangement of the other substituants is designated as Cis (c) or trans (t) relative to the reference substituent. See ref 1g, page 1382.
34. Carey, F. A.; Tremper, H. S. J. Org. Chem. 1971, 36, 758.
35. If the reaction is conducted using commercially available PhLi, the use of fresh reagent is recommended.
36. Preliminary X-ray data corroborate this structural assignment.
37. A lower limit for the exchange rate at 418 K was estimated using the Gutowsky-Holm equation: Gutowsky, H. S.: Holm, C. H. J. Chem. Phys. 1956, 25, 1228.
38. Two, four, three, and one t-Bu signals are expected for 8a, 8b, 8c. and 8d, respectively, assuming a 1,3-alternate conformation of the macro-cycle in all forms.
39. The second crop of crystals afforded a sample of the rctc isomer in 81% purity.
40. 3/acetonitrile affords mainly the rctt form.
41. 2 = 0.1804.
42. Because the methine protons of 9 are located at axial positions, the phenyl groups at the bridges must be located at equatorial ones.