Lewis acid-nitromethane complex-promoted Friedel-Crafts reactions of PS-DVB-resins

Tetrahedron Letters

Volumn 47, Issue 49, 2006, Pages 8711-8715

  Zikos, Christos ^a,b,c   Alexiou, George ^a,b   Ferderigos, Nicolas ^a,b  

^a UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^c Biomedica Life Sciences SA   (Greece)

Author keywords

Friedel Crafts alkylation; Peptides; Solid phase synthesis

Indexed keywords

ACYL CARRIER PROTEIN; FERRIC CHLORIDE; LEWIS ACID; NITROMETHANE; PEPTIDE; POLYSTYRENE DERIVATIVE; RESIN;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; PROTEIN SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750470084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.033     Document Type: Article

References (32)

1. Olah G.A. Friedel-Crafts Chemistry (1973), Wiley-Interscience, New York
2. Smith M.B. Organic Synthesis (1994), McGraw-Hill, New York
3. Heaney H. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York 733
4. Lowry T.H., and Richardson K.S. Mechanism and Theory in Organic Chemistry. 3rd ed. (1987), Harper and Row, New York p 626
5. White E.H. Tetrahedron Lett. 38 (1997) 7649
6. Darbean R.W., and White E.H. J. Org. Chem. 65 (2000) 1121-1131 and references cited therein
7. Olah G.A., Kabayashi S., and Tashiro M. J. Am. Chem. Soc. 94 (1972) 7448-7461
8. Olah G.A., Kuhn S.J., and Flood S.H. J. Am. Chem. Soc. 84 (1962) 1688-1695
9. Feinberg R.S., and Merrifield R.B. Tetrahedron 30 (1974) 3209-3212
10. Mitchell A.R., Kent S.B.H., Erickson B.W., and Merrifield R.B. Tetrahedron Lett. 42 (1976) 3795-3798
11. Mitchell A.R., Kent S.B.H., Engelhard M., and Merrifield R.B. J. Org. Chem. 43 (1978) 2845-2852
12. Hider, R. C.; Goodwin, B. L. PCT Int. Patent 96/25440, 1996; Chem. Abstr. 1996, 125, 248887.
13. Zikos C.C., and Ferderigos N.G. Tetrahedron Lett. 36 (1995) 3741-3744
14. Park B.-D., Lee H.-I., Ryoo S.-J., and Lee Y.-S. Tetrahedron Lett. 38 (1997) 591-594
15. Bevacqua F., Basso A., Gitto R., Bradley M., and Chimirri A. Tetrahedron Lett. 42 (2001) 7683-7685
16. Sherrington D.C. Chem. Commun. (1998) 2275-2286
17. Jones B. Ind. Eng. Chem. 44 (1952) 2686
18. Adams J.H., Cook R.M., Hudson D., Jammalamadaka V., Lyttle M.H., and Songster M. J. Org. Chem. 63 (1998) 3706-3716
19. Pugh K.C., York E.J., and Stewart J.M. Int. J. Pept. Protein Res. 40 (1992) 208
20. Hodge P.C., and Sherrington D.C. Polymer-supported Reactions in Organic Chemistry (1988), Wiley, Chichester
21. Meldal M. In: Fields G. (Ed). Solid-phase Peptide Synthesis (1998), Academic Press, New York 83-104
22. Radmann J., Grötli M., Mendal M., and Bock K. J. Am. Chem. Soc. 121 (1999) 5459-5466
23. -1 had disappeared.
24. Cavalli G., Shooter A.G., Pears A.D., and Steinke H.G. J. Comb. Chem. 5 (2003) 637-644
25. Rademann J., Barth M., Brock R., Egelhaaf H.-J., and Jung G. Chem. Eur. J. 7 (2001) 3884-3889
26. A mixture of Fmoc-β-alanine (0.02 equiv) and benzoic acid (0.98 equiv) was activated by DIC/HOBt for 15 min and then added to each AMPS resin (50 mg, 1 mmol/g). After 20 h the resins were washed with DMF (4 × 1 mL), the Fmoc group was removed with piperidine/DMF (20%), then a pyridine solution of fluorescein isothiocyanate (4 equiv) was added and the reaction left overnight. Upon completion of the reaction, the resins were washed thoroughly with pyridine, DCM and ether and dried in vacuo. The beads were sliced (5 μm) using a Leica microtome. Fluorescence microscopy was conducted with a Nicon ECLIPSE E400 epifluorescence microscope. The excitation of the fluorescence was effected by a super high pressure mercury lamp. The images were recorded with a PCO Sensicam Super VGA camera. For all measurements a 10 × 0.25 objective lens was used.
27. Gerritz S.W. Curr. Opin. Chem. Biol. 5 (2001) 264-268
28. Rink H. Tetrahedron Lett. 28 (1987) 3787-3790
29. Chang C.D., Waki M., Ahmad M., Meienhofer J., Lundell E.O., and Haug J.D. Int. J. Pept. Protein Res. 15 (1980) 59
30. Hancock W.S., Prescott D.J., Vagelos P.R., and Marshall G.R. J. Org. Chem. 38 (1973) 774
31. Johnson T.J., Quibell M., Owen D., and Sheppard R.C. J. Chem. Soc., Chem. Commun. (1993) 369
32. Meisenbach M., Allmendinger T., and Mak C.P. Org. Process Res. Dev. 7 (2003) 553-558