Amino-acid templated assembly of sucrose-derived macrocycles

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2532-2535

  Lewandowski, Bartosz ^a   Jarosz, Slawomir ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ETHYLENEDIAMINE; ETHYLENEDIAMINE DERIVATIVE; MACROCYCLIC COMPOUND; SUCROSE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMINO ACIDS; CATALYSIS; CYCLIZATION; ETHYLENEDIAMINES; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; SUCROSE;

EID: 77952990801     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100749m     Document Type: Article

References (23)

1. Breinbauer, R.; Vetter, I. R.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878-2881
2. Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-516
3. Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. Nat. Rev. 2008, 7, 608
4. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, 1995.
5. Supramolecular Chemistry; Vogtle, F., Ed.; Wiley & Sons: Chichester, 1991.
6. Ziegler, K.; Eberle, H.; Ohlinger, H. Liebigs Ann Chim. 1933, 504, 94-130
7. Pietraszkiewicz, M.; Salanski, P.; Jurczak, J. J. Chem. Soc., Chem. Commun. 1983, 1184-1185
8. Template Synthesis of Macrocyclic Compounds; Gerbeleu, N. V.; Arion, V. B.; Burgess, J., Eds.; Wiley-VCH: Weinheim, 1999.
9. Busch, D. H.; Vance, A. L.; Kolchinski, G. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Elsevier Science: New York, 1996; Vol. 9, pp 1 - 42.
10. For comprehensive review, see
11. Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vogtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 11.
12. Brzuszkiewicz, A.; Ciunik, Z.; Jarosz, S.; Lewandowski, B.; Listkowski, A. Tetrahedron 2005, 61, 8485-8492
13. Jarosz, S.; Lewandowski, B. Carbohydr. Res. 2008, 5, 965-969
14. Queneau, Y.; Jarosz, S.; Lewandowski, B.; Fitremann, J. Adv. Carbohydr. Chem. Biochem. 2007, 61, 217-292
15. Jarosz, S.; Listkowski, A. J. Carbohydr. Chem. 2003, 22, 753-763
16. Jarosz, S.; Lewandowski, B. Chem. Commun. 2008, 6399-6341
17. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2007
18. Tornoe, C. M.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
19. Jarosz, S.; Lewandowski, B.; Listkowski, A. Synthesis 2008, 913-917
20. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
21. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855
22. 3 (500 mg), phenylglycine methyl ester hydrochloride HCl (25 mg) and ethylenediamine (0.02 mL) were added. The mixture was refluxed for 48 h. After being cooled to rt, the mixture was partitioned between water (5 mL) and ethyl acetate (15 mL), the layers were separated, the organic layer was dried and concentrated, and the product was isolated by column chromatography (toluene-methanol 15:1 for 16 or toluene-methanol 12:1 then 5:1 for 17).
23. Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135