Design and synthesis of a new class of nonmacrocyclic alkali metal host compounds

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3453-3456

  McGarvey, Glenn J ^a   Stepanian, Marshall W ^a   Bressette, Andrew R ^a   Sabat, Michal ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009147056     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006468o     Document Type: Article

References (30)

1. For reviews, see: (a) Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vogtle, F., Gokel, G. W., Eds. Comprehensive Supramolecular Chemistry, Vol. 1; Pergamon: Oxford, 1996.
2. (b) Izatt, R. M.; Pawluk, G. W.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529.
3. (c) Gokel, G., Crown Ethers and Cryptands; The Royal Society of Chemistry: Cambridge, UK, 1991.
4. For a recent review, see: Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2055, and relevant references therein.
5. Westley, J. W., Polyether Antibiotics: Naturally Occurring Acid Ionophores, Vois. 1 and 2: Marcel Dekker: New York, 1983.
6. For particularly pertinent examples, see: (a) Li, G.; Still, W. C. Tetrahedron Lett. 1993, 34, 919.
7. (b) Erickson, S. D.; Still, W. C. Tetrahedron Lett. 1990, 31, 4253.
8. (c) Iimori, T.; Still, W. C.; Rheingold, A. L.; Staley, D. L. J. Am. Chem. Soc. 1989, 111, 3439.
9. Angyal, S. J. Adv. C arbohydr. Chem. Biochem. 1989, 47, 1.
10. Hegetschweiler, K. Chem. Soc. Rev. 1999, 28, 239.
11. (a) Negri, J. T.; Rogers, R. D.; Paquette, L. A. J. Am. Chem. Soc. 1991, 113, 5073.
12. (b) Paquette, L. A.; Tae, J.; Hinkey, E. R.; Rogers, R. D. Angew. Chem., Int. Ed. 1999, 38, 1409.
13. (c) Tae, J.; Rogers, R. D.; Paquette, L. A. Org. Lett. 2000, 2, 138.
14. (d) Paquette, L. A.; Tae, J.; Gallucci, J. C. Org. Lett. 2000, 2, 143. (NOTE: Compound 3 is depicted in its most stable, uncomplexed conformation.)
15. (a) McGarvey, G. J.; Stepanian, M. W. Tetrahedron Lett. 1996, 31, 5461.
16. (b) McGarvey, G. J.; Stepanian, M. W.; Bressette, A. R.; Ellena, J. F. Tetrahedron Lett. 1996, 37, 5465.
17. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry: Pergamon: Oxford, 1983.
18. (b) The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R., Ed.; ACS Symp. Series 539; American Chemical Society: Washington, DC, 1993.
19. Lithiation of dihydropyran: Amouroux, R. Heterocycl. 1984, 22, 1489. Cuprate formation: Kozlowski, J. A.; Lipshutz, B. H.; Wilhelm, R. S. Tetrahedron 1984, 24, 5005.
20. Lithiation of dihydropyran: Amouroux, R. Heterocycl. 1984, 22, 1489. Cuprate formation: Kozlowski, J. A.; Lipshutz, B. H.; Wilhelm, R. S. Tetrahedron 1984, 24, 5005.
21. The spirocyclization reaction has been routinely carried out on more than 10 g of precursor 9 to afford approximately 5 g of anti-10c after a single recycle.
22. A modified procedure was used: Danishefsky, S. J.; Jeroncic, L. O.; Linde, R. G. J. Org. Chem. 1991, 56, 2534.
23. 4 gave a 23:39:38 mixture of 10t:syn-10c: anti-10c.
24. Crabbe, P.; Drian, C. L.; Greene, A. E. J. Am. Chem. Soc. 1980, 102, 7583.
25. The hydrogens have been omitted for clarity.
26. Ipaktschi, J. Chem. Ber. 1984, 117, 856.
27. Cowen, K. A.; Leuck, D. J.; Mattson, R. J.; Pham, K. M. J. Org. Chem. 1990, 55, 2552.
28. Cram, D. J.; Kaneda, T.; Koenig, K. E.; Lein, G. M.; Stuckler, LP. J. Am. Chem. Soc. 1979, 101, 3553.
29. The association constants obtained were in good agreement with those reported in other studies. See refs 4c and 18.
30. It is noteworthy that Paquette and co-workers observed similarly poor host characteristics with a triaxial 1,3,5-trimethoxycyclohexane derivative. See ref 4c.