Template-Directed Ring-Closing Metathesis: Synthesis and Polymerization of Unsaturated Crown Ether Analogs

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 10, 1997, Pages 1101-1103

  Marsella, Michael J ^a   Maynard, Heather D ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

Crown compounds; Cyclizations; Homogeneous catalysis; Metathesis; Template synthesis

Indexed keywords

EID: 0030791288     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711011     Document Type: Article

References (21)

1. a) Review of ring closure: G. Illuminati, L. Mangolini, Acc. Chem. Res. 1981, 14, 95.
2. Recent reviews and examples of RCM: b) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446.
3. c) H.-G. Schmalz, Angew Chem. 1995, 97, 1981; Angew. Chem. Int. Ed. Engl. 1995, 34, 1833.
4. c) H.-G. Schmalz, Angew Chem. 1995, 97, 1981; Angew. Chem. Int. Ed. Engl. 1995, 34, 1833.
5. d) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolau, ibid. 1997, 109, 170 and 1997, 36, 166.
6. d) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolau, ibid. 1997, 109, 170 and 1997, 36, 166.
7. e) A. Fürstner, N. Kindler, Tetrahedron Lett. 1996, 37, 7005.
8. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
9. Examples of RCM utilizing hydrogen bonding: a) S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855. b) T. D. Clark, M. R. Ghadiri, ibid. 1995, 117, 12364. c) S. J. Miller, H. E. Blackwell, R. H. Grubbs, ibid. 1996, 118, 9606.
10. Examples of RCM utilizing hydrogen bonding: a) S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855. b) T. D. Clark, M. R. Ghadiri, ibid. 1995, 117, 12364. c) S. J. Miller, H. E. Blackwell, R. H. Grubbs, ibid. 1996, 118, 9606.
11. Examples of RCM utilizing hydrogen bonding: a) S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855. b) T. D. Clark, M. R. Ghadiri, ibid. 1995, 117, 12364. c) S. J. Miller, H. E. Blackwell, R. H. Grubbs, ibid. 1996, 118, 9606.
12. Examples of RCM of conformationally constrained dienes: S. J. Miller, S. H. Kim, Z. R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
13. M. D. E. Forbes, J. T. Patton, T. L. Myers, H. D. Maynard, D. W. Smith, G. R. Shultz, K. B. Wagener, J. Am. Chem. Soc. 1992, 114, 10978.
14. Examples of RCM devoid of conformational constraints: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942.
15. Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1989.
16. Report of 3 (n = 2) prepared in the absence of a template: B. König, C. Horn, Synlett, 1996, 1013.
17. a) K. J. Ivin, Olefin Metathesis, Academic Press, London, 1997.
18. b) Z. R. Chen, J. P. Claverie, R. H. Grubbs, J. A. Kornfield, Macromolecules 1995, 28, 2147.
19. 2/ MeOH with LiCl failed to yield 3 (n = 1) and instead provided predominantly the same isomerization product that was observed in the ADMET of 2 (n=1): C. Fraser, R. H. Grubbs, unpublished results.
20. RCM has been used to synthesize other supramolecular systems in high yield: B. Mohr, M. Weck, J.-P. Sauvage, R. H. Grubbs, Angew. Chemie. 1997, 109, no. 12; Angew. Chem. Int. Ed. Engl. 1997, 109, no. 12.
21. RCM has been used to synthesize other supramolecular systems in high yield: B. Mohr, M. Weck, J.-P. Sauvage, R. H. Grubbs, Angew. Chemie. 1997, 109, no. 12; Angew. Chem. Int. Ed. Engl. 1997, 109, no. 12.