ROMPGEL Scavengers: A high-loading supported anhydride for sequestering amines and hydrazines

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2663-2666

  Arnauld, Thomas ^a   Barrett, Anthony G M ^a   Cramp, Susan M ^b   Roberts, Richard S ^a   Zécri, Frederic J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Avenus CropScience   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037916293     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006191s     Document Type: Article

References (32)

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3. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527.
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5. (e) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385.
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7. (b) Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. Curr. Opin. Chem. Biol. 1999, 3, 320.
8. (c) Bunin, B. A. The Combinatorial Index: Academic press: San Diego. CA, 1998.
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10. (a) Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874.
11. (b) Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882.
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13. The Combinatorial Chemistry Catalog, March. 1999; Novabiochem Corp.; pp 1-3, S63, S66-7
14. Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 39, 1121.
15. Coppola, G. M. Tetrahedron Lett. 1998, 39, 8233.
16. Zhu, D. W. Macromolecules 1996, 29, 2813.
17. Hodges, J. C.; Harikrishnan, L. S.; Ault-Justus, S. J. Comb. Chem. 2000, 2, 80.
18. (a) Shuker, A. J.; Siegel, M. G.; Matthews, D. P.; Weigel, L. O. Tetrahedron Lett. 1997, 38, 6149.
19. (b) Laurence, R. M.; Biller, S. A.; Frysman, O. M.; Poss, M. A. Synthesis 1997, 553.
20. (a) Parlow, J. J.; Mischke, D. A.; Woodard, S. S. J. Org. Chem. 1997, 62, 5908.
21. (b) Parlow, J. J.; Naing, W.; South, M. S.; Flynn, D. L. Tetrahedron Lett. 1997, 38, 7959.
22. (c) Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
23. Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357.
24. (a) For ROMPGEL Horner - Emmons reagent, see: Barren, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zécri, F. J. Org. Lett. 1999, 1, 579.
25. (b) For ROMPGEL acylation reagent, see: Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zécri, F. J. Org. Lett. 2000, 2, 261.
26. (c) For ROMPGEL synthesis of 1,2,4-oxadiazoles, see: Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zécri, F. J. Comb. Chem. High Throughput Screening 2000, 3, 131.
27. Catalyst is commercially available from Fluka. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
28. Kanaoka, S.; Grubbs, R. H. Macromolecules 1995, 28, 4707.
29. Buchmeiser, M. R.; Atzl, N.; Bonn, G. K. J. Am. Chem. Soc. 1997, 119, 9166.
30. Typical procedure: To a solution of isocyanate (0.25 mmol) in methylene chloride (3 mL) was added the amine (0.75 mmol). The solution was stirred at room temperature for 3 h before addition of 70 mg of ROMPGEL scavenger 2 (0.75 mmol). The suspension was stirred at room temperature for 3 h, filtered off, and washed with methylene chloride (2 × 3 mL). The solvent was then removed in a stream of nitrogen to give the desired urea.
31. Arcadi, A.; Marinelli, F.; Bernocchi, E.; Cacchi, S.; Ortar, G. J. Organomet. Chem. 1989, 368, 249.
32. Xu, W.; Mohan, R.; Morrissey, M. M. Tetrahedron Lett. 1997, 38, 7337.