Optimized synthesis of hydrogen-bond surrogate helices: Surprising effects of microwave heating on the activity of grubbs catalysts

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5825-5828

  Chapman, Ross N ^a   Arora, Paramjit S ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINO ACID; PEPTIDE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MICROWAVE RADIATION; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

ALKENES; AMINO ACIDS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; HEAT; HYDROGEN BONDING; MICROWAVES; PEPTIDES; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SOLVENTS;

EID: 33846285239     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062443z     Document Type: Article

References (25)

1. (a) Wang, D.; Chen, K.; Kulp, J. K., III; Arora, P. S. J. Am. Chem. Soc. 2006, 128, 9248-9256.
2. (b) Chapman, R. N.; DiMartino, G.; Arora, P. S. J. Am. Chem. Soc. 2004, 126, 12252-12253.
3. (a) Shepherd, N. E.; Abbenante, G.; Fairlie, D. P. J. Am. Chem. Soc. 2005, 127, 2974-2983.
4. (b) Schafmeister, C. E.; Po, J.; Verdine, G. L. J. Am. Chem. Soc. 2000, 122, 5891-5892.
5. (c) Blackwell, H. E.; Grubbs, R. H. Angew. Chem., Int. Ed. 1998, 37, 3281-3284.
6. Wang, D.; Liao, W.; Arora, P. S. Angew. Chem., Int. Ed. 2005, 117, 6683-6687.
7. DiMartino, G.; Wang, D.; Chapman, R. N.; Arora, P. S. Org. Lett. 2005, 7, 2389-2392.
8. (a) Armen, R.; Alonso, D. O. V.; Daggett, V. Protein Sci. 2003, 12, 1145-1157.
9. (b) Fodje, M. N.; Al-Karadaghi, S. Protein Eng. 2002, 15, 353-358.
10. (c) Bolin, K. A.; Millhauser, G. L. Acc. Chem. Res. 1999, 32, 1027-1033.
11. (a) Bowman, M. D.; Jacobson, M. M.; Pujanauski, B. G.; Blackwell, H. E. Tetrahedron 2006, 62, 4715-4727.
12. (b) Murray, J. K.; Farooqi, B.; Sadowsky, J. D.; Scalf, M.; Freund, W. A.; Smith, L. M.; Chen, J. D.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13271-13280.
13. (c) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
14. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
15. (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
16. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
17. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, P. A. Org. Biomol. Chem. 2004, 2, 8-23.
18. Van Der Schaaf, P. A.; Kolly, R.; Kirner, H.; Rime, F.; Muhlebach, A.; Hafner, A. J. Organomet. Chem. 2000, 606, 65-74.
19. The microwave reactions were performed in the CEM Discover single-mode reactor with controlled power, temperature, and time settings.
20. (a) Garbacia, S.; Desai, B.; Lavastre, O.; Kappe, C. O. J. Org. Chem. 2003, 68, 9136-9139.
21. (b) Mayo, K. G.; Nearhoof, E. H.; Kiddle, J. Org. Lett. 2002, 4, 1567-1570.
22. Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794-796.
23. (a) Bock, V. D.; Perciaccante, R.; Jansen, T. P.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2006, 8, 919-9122.
24. (b) Meutermans, W. D. F.; Bourne, G. T.; Golding, S. W.; Horton, D. A.; Campitelli, M. R.; Craik, D.; Scanlon, M.; Smythe, M. L. Org. Lett. 2003, 5, 2711-2714.
25. Optimum microwave conditions: Bisolefins in Figures 4 and 5 were irradiated with microwaves with 15 mol % of GII for 2 min at 120 °C in dichlorobenzene or with 15 mol % of HGII for 5 min at 200 °C in dichlorobenzene. Optimum oil-bath conditions: 72 h at 50 °C with 15 mol % of GII or HGII catalysts in dichloroethane.