Monolithiocavitands: Versatile intermediates for new cavitand-based hosts

Organic Letters

Volumn 3, Issue 2, 2001, Pages 225-227

  Irwin, Jacob L ^a   Sherburn, Michael S ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

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ARTICLE;

EID: 0000155271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006881w     Document Type: Article

References (35)

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3. (a) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
4. (b) Warmuth R. J. Inclusion Phenom. Mol. Recognit. Chem. 2000, 37, 1-38.
5. (a) Kobayashi, K.; Shirasaka, T.; Yamaguchi, K.; Sakamoto, S.; Horn, E.; Furukawa, N. Chem. Commun. 2000, 41-42.
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8. (d) Chapman, R. G.; Olovsson, G.; Trotter, J.; Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260.
9. Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1998, 2689-2702.
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16. (a) Hamada, F.; Ito, S.; Narita, M.; Nashirozawa, N. Tetrahedron Lett. 1999, 40, 1527.
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19. (d) Boerrigter, H.; Verboom, W.; Reinhoudt, D. N. Liebigs Ann./Recueil. 1997, 2247-2254.
20. (e) van Wageningen, A. M. A.; Snip, E.; Verboom, W.; Reinhoudt, D. N.; Boerrigter, H. Liebigs Ann./Recueil 1997, 2235-2245.
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22. (g) Peinador, C.; Roman, E.; Abboud, K.; Kaifer, A. E. Chem. Commun. 1999, 1887-1888.
23. (h) A,B-Difunctionalized bowls have been prepared in nonstatistical yields through the ingenious (if somewhat lengthy) derivatization of triply bridged resorcinarenes: Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191; Sorrell, T. N.; Richards, J. L. Synlett 1992, 155-156.
24. (h) A,B-Difunctionalized bowls have been prepared in nonstatistical yields through the ingenious (if somewhat lengthy) derivatization of triply bridged resorcinarenes: Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191; Sorrell, T. N.; Richards, J. L. Synlett 1992, 155-156.
25. Irwin, J. L.; Sherburn, M. S. J. Org. Chem. 2000, 65, 602-605.
26. Irwin, J. L.; Sherburn, M. S. J. Org. Chem. 2000, 65, 5846-5848.
27. See the Supporting Information for full details.
28. The monosubstituted product comprises ca. 80% of the product mixture.
29. Yield optimization and guest binding studies with 18 are under way.
30. We noted a similar result in the preparation of 4a; see ref 8.
31. For examples of inherently chiral cavitands resulting from unsymmetrical bridging arrangements, see: (a) Cram, D. J.; Tunsted, L. M.; Knobler, C. B. J. Org. Chem. 1992, 57, 528-535.
32. (b) Soncini, P.; Bonsignore, S.; Dalcanale, E.; Ugozzoli, F. J. Org. Chem. 1992, 57, 4608-4612. We thank a referee for drawing our attention to these papers.
33. For chiral cavitands formed by appending stereogenic moieties to the bowl, see: Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994.
34. For cycloenantioisomerism in self-folding, deep cavity cavitands, see: Lucking, U.; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 2000, 122, 8880-8889 and references therein.
35. Attempted separation of the enantiomers of 22 on chiral HPLC columns have thus far proved unsuccessful. Efforts are ongoing in this regard.