Lewis super-acid catalyzed cyclizations: A new route to fragrance compounds

Chemistry and Biodiversity

Volumn 5, Issue 6, 2008, Pages 1070-1082

  Coulombel, Lydie ^a   Grau, Fanny ^a   Weïwer, Michel ^a   Favier, Isabelle ^a   Chaminade, Xavier ^a   Heumann, Andreas ^b   Bayón, J Carles ^c   Aguirre, Pedro A ^c   Duñach, Elisabet ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE DERIVATIVE; ALKENE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; ETHER DERIVATIVE; FRAGRANCE; LACTONE DERIVATIVE; LEWIS ACID; PHOSPHITE; THIOACID; THIOL DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; ALCOHOL DERIVATIVE; CARBOXYLIC ACID; CYCLOHEXANONE DERIVATIVE; MESYLIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; PERFUME; TRIFLIMIDE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROFORMYLATION; ISOMERIZATION; ODOR; REVIEW; SMELLING; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; STEREOISOMERISM;

ALCOHOLS; CARBOXYLIC ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; CYCLIZATION; CYCLOHEXANONES; MESYLATES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PERFUME; STEREOISOMERISM;

EID: 52649092925     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200890086     Document Type: Review

References (50)

1. 'Lewis Acids in Organic Synthesis', Ed. H. Yamamoto, 2 Vol., Wiley-VCH, Weinheim, 2000.
2. S. Kobayashi, Eur. J. Org. Chem. 1999, 15;
3. C. Hahn, Chem.-Eur. J. 2004, 10, 5888.
4. R. J. Gillespie, T. E. Peel, J. Am. Chem. Soc. 1973, 95, 5173.
5. J. Nie, J. Xu, G. Zhou, J. Chem. Res., Synop. 1999, 446;
6. P. A. Grieco, S. T. Handy, Tetrahedron Lett. 1997, 38, 2645;
7. A. Vij, Y. Y. Zheng, R. L. Kirchmeier, J. M. Shreeve, Inorg. Chem. 1994, 33, 3281.
8. I. Favier, E. Duñach, Tetrahedron Lett. 2003, 44, 2031;
9. E. Duñach, I. Favier, D. Hebrault, J. R. Desmurs, to Rhodia Chimie, FR Pat. 2818994, 2002.
10. A. P. S. Narula, Perfum. Flavor. 2003, 28(4), 62.
11. M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya,V. A. Barkhash,V. B. Perutskii, N. D. Ungur, P. F. Vlad, V. V. Shcherbukhin, N. K. Zefirov, J. Org. Chem. 1994, 59, 1509;
12. L. Coulombel, E. Duñach, Green Chem. 2004, 6, 499; P D. Noire, US Pat. Appl. 5510326 A (Chem. Abstr. 1996, 125, 86473);
13. A. P. S. Narula, E. M. Arruda, US Pat. Appl. 2004110991 A1 (Chem. Abstr. 2004, 141, 38754).
14. M. L. Mihailovic, Z. Petrovic, A. Teodorovic, S. Konstantinovic, V. Andrejevic, C. R. Acad. Sci. Paris 1989, 308, 29.
15. L. Coulombel, I. Favier, E. Duñach, Chem. Commun. 2005, 2286.
16. L. Coulombel, M. Rajzmann, J. M. Pons, S. Olivero, E. Duñach, Chem.-Eur. J. 2006, 12, 6356.
17. L. Coulombel, E. Duñach, Synth. Commun. 2005, 35, 153.
18. X. Chaminade, L. Coulombel, S. Olivero, E. Duñach, Eur. J. Org. Chem. 2006, 3554.
19. A. J. A. van der Weerdt, R. Plomp, W. Apeldoorn, to Naarden International, Eur. Pat. Appl. 49543 A1 (Chem. Abstr. 1982, 97, 60836).
20. L. Dufosse, A. Latrasse, H. E. Spinnler, Sci. Aliments 1994, 14, 17.
21. A. Goeke, Sulfur Reports 2002, 23, 243.
22. S. B. Jameson, in 'Chemistry and Technology of Flavors and Fragrances', Ed. D. J. Rowe, Blackwell Publishing, Oxford, 2005.
23. K. Griesbaum, Angew. Chem., Int. Ed. 1970, 9, 273.
24. C. G. Screttas, M. Micha-Screttas, J. Org. Chem. 1979, 44, 713;
25. F. Wolf, H. Finke, Z. Chem. 1972, 12, 180;
26. S. Kanagasabapathy, A. Sudalai, B. C. Benicewicz, Tetrahedron Lett. 2001, 42, 3791.
27. T. Mukaiyama, T. Izawa, K. Saigo, H. Takei, Chem. Lett. 1973, 355;
28. M. Belley, R. Zamboni, J. Org. Chem. 1989, 54, 1230.
29. M. Weïwer, L. Coulombel, E. Duñach, Chem. Commun. 2006 , 332.
30. M. Weïwer, E. Duñach, Tetrahedron Lett. 2006, 47, 287.
31. D. Prajapati, D. D. Laskar, J. S. Sandhu, Tetrahedron Lett. 2000, 41, 8639;
32. R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, J. Mol. Catal. A: Chem. 2004, 215, 49.
33. M. Weïwer, X. Chaminade, J. C. Bayon, E. Duñach, Eur. J. Org. Chem. 2007, 2464.
34. T. L. Ho, 'Carbocycle Construction in Terpene Synthesis', Wiley-VCH, Weinheim, 1988.
35. B. M. Trost, Acc. Chem. Res. 1990, 23, 34.
36. S. Okamoto, T. Livinghouse, Organometallics 2000, 19, 1449;
37. S. Thiele, G. Erker, Chem. Ber. 1997, 130, 201;
38. K. H. Shaughnessy, R. M. Waymouth, J. Am. Chem. Soc. 1995, 117, 5873;
39. W. E. Piers, P. J. Shapiro, E. E. Bunel, J. E. Bercaw, Synlett 1990, 74;
40. P.W. Chum, S. E. Wilson, Tetrahedron Lett. 1976, 1257.
41. F. Grau, A. Heumann, E. Duñach, Angew. Chem. 2006, 118, 7443;
42. Angew. Chem., Int. Ed. 2006, 45, 7285.
43. H. Surburg, J. Panten, 'Common Fragrance and Flavor Materials: Preparation, Properties and Uses', 5th edn., Wiley-VCH, Weinheim, 2006;
44. C. S. Sell, 'A Fragrant Introduction to Terpenoid Chemistry', RSC, Cambridge, 2003.
45. P. Kraft, J. A. Bajgrowicz, C. Denis, G. Fráter, Angew. Chem. 2000, 112, 3106;
46. Angew. Chem., Int. Ed. 2000, 39, 2980;
47. G. Fráter, J. A. Bajgrowicz, P. Kraft, Tetrahedron 1998, 54, 7633;
48. C. S. Sell, 'The Chemistry of Fragrances', 2nd edn., RSC Paperbacks, Cambridge, 2006.
49. J. C. Chalchat, R. P. Garry, E. Lecomte, A. Michet, Flavour Fragr. J. 1991, 6, 179.
50. F. Grau, J. C. Bayón, P. A. Aguirre, T. Parella, E. Duñach, Eur. J. Org. Chem. 2008, 7, 1214.