Macrocyclization and molecular interlocking via Mitsunobu alkylation: Highlighting the role of C-H⋯O interactions in templating

Organic Letters

Volumn 2, Issue 4, 2000, Pages 449-452

  Hansen, Jimmi G ^a,b   Feeder, Neil ^a   Hamilton, Darren G ^a   Gunter, Maxwell J ^a,c   Becher, Jan ^b   Sanders, Jeremy K M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001182110     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991289w     Document Type: Article

References (17)

1. Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620.
2. Hamilton, D. G.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. New J. Chem. 1998, 22, 1019-1021.
3. Try, A. C.; Harding, M. M.; Hamilton, D. G.; Sanders, J. K. M. Chem. Commun. 1998, 723-724.
4. Hansen, J. G.; Bang, K. S.; Thorup, N.; Becher, J. Eur. J. Org. Chem., in press.
5. Ashton, P. R.; Huff, J.; Menzer, S.; Parsons, I. W.; Preece, J. A.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 31-44.
6. Lebeau, L.; Oudet, P.; Mioskowski, C. Helv. Chim. Acta 1991, 74, 1697-1706.
7. Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1995, 2223-2229.
8. Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399.
9. Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
10. Houk, K. N.; Menzer, S.; Newton, S. P.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 1479-1487.
11. Steiner, T. Chem. Commun. 1997, 727-734.
12. 2 grouping, see: Ashton, P. R.; Huff, J.; Menzer, S.; Parsons, I. W.; Preece, J. A.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 31-44.
13. We had previously attempted to prepare more soluble analogues of [2]catenane 3 by equipping the diimide precursor with solubilizing ethyl groups in place of the methylene hydrogens, see: Hamilton, D. G.; Prodi, L.; Feeder, N.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1999, 1057-1065. No interlocked products were obtained from these reactions, and the product distribution from cyclizations of this modified diimide could not be influenced in any way with electron-rich template molecules. We attributed this failure to an inability of the soluble diimide to achieve a favorable donor-acceptor overlap geometry with electron-rich substrates as a result of the inclusion of bulky alkyl substituents. In light of the current results this failure may have as much, or rather more, to do with the absence of acidic methylene hydrogens occasioned by the inclusion of the additional alkyl groups.
14. Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. Eur. J. 2000, 6, 608-617.
15. Hamilton, D. G.; Lynch, D. E.; Byriel, K. A.; Kennard, C. H. L. Aust. J. Chem. 1997, 50, 439-445.
16. Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303-305.
17. The capacity to form C-H⋯O contacts is partly a consequence of having "acidic" protons available, i.e. protons attached to electron-deficient systems. Accordingly, and rather by default, successful systems are likely to contain electron-deficient components (to provide the "acidic" protons) and electron-rich donor sites such as oxygen atoms.