Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent

Tetrahedron Letters

Volumn 44, Issue 35, 2003, Pages 6651-6655

  Linares Palomino, Pablo J ^a   Salido, Sofía ^a   Altarejos, Joaquín ^a   Sánchez, Adolfo ^a  

^a UNIVERSITY OF JAÉN   (Spain)

Author keywords

Benzopyrans; Chlorosulfonic acid; Electrophilic olefin cyclization; Odorants; Sulfonic acids

Indexed keywords

CHLOROSULFONIC ACID; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; SCALE UP; STEREOCHEMISTRY;

EID: 0042671133     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01635-6     Document Type: Article

References (29)

1. Sutherland, J. K. In Polyene Cyclizations; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Comprehensive organic synthesis; Pergamon Press: Oxford, 1991; Vol. 3, pp. 341-377.
2. For recent and key papers, see: (a) Ungur, N.; Kulcitki, V.; Gavagnin, M.; Castellucio, F.; Vlad, P. F.; Cimino, G. Tetrahedron 2002, 58, 10159-10165 and references cited therein; (b) Vlad, P. F. Pure Appl. Chem. 1993, 65, 1329-1336 and references cited therein; (c) Snowden, R. L.; Eichenberger, J.-C.; Linder, S. M.; Sonnay, P.; Vial, C.; Schulte-Elte, K. H. J. Org. Chem. 1992, 57, 955-960.
3. For recent and key papers, see: (a) Ungur, N.; Kulcitki, V.; Gavagnin, M.; Castellucio, F.; Vlad, P. F.; Cimino, G. Tetrahedron 2002, 58, 10159-10165 and references cited therein; (b) Vlad, P. F. Pure Appl. Chem. 1993, 65, 1329-1336 and references cited therein; (c) Snowden, R. L.; Eichenberger, J.-C.; Linder, S. M.; Sonnay, P.; Vial, C.; Schulte-Elte, K. H. J. Org. Chem. 1992, 57, 955-960.
4. For recent and key papers, see: (a) Ungur, N.; Kulcitki, V.; Gavagnin, M.; Castellucio, F.; Vlad, P. F.; Cimino, G. Tetrahedron 2002, 58, 10159-10165 and references cited therein; (b) Vlad, P. F. Pure Appl. Chem. 1993, 65, 1329-1336 and references cited therein; (c) Snowden, R. L.; Eichenberger, J.-C.; Linder, S. M.; Sonnay, P.; Vial, C.; Schulte-Elte, K. H. J. Org. Chem. 1992, 57, 955-960.
5. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995.
6. Cremlyn R.J. Chlorosulfonic Acid: A Versatile Reagent. 2002;Royal Society of Chemistry, Cambridge.
7. Oritani, T.; Yamashita, K. JP 02258773 [Chem. Abstr. 1990, 114, 143747].
8. Imamura P.M., Santiago G.M.P. Synth. Commun. 27:1997;2479-2485.
9. For some references, see: (a) Schlummer, B.; Hartwig, J. F. Org. Lett. 2002, 4, 1471-1474; (b) Erman, M. B.; Hoffmann, H. M.; Cárdenas, C. G. EP 985651 [Chem. Abstr. 2000, 132, 207981]. For an example of bicyclization, see: (c) Muntyan, G. E.; Kurbanov, M.; Smit, V. A.; Semenovskii, A. V.; Kucherov, V. F. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 633-639 [Chem. Abstr. 1973, 79, 18869f].
10. For some references, see: (a) Schlummer, B.; Hartwig, J. F. Org. Lett. 2002, 4, 1471-1474; (b) Erman, M. B.; Hoffmann, H. M.; Cárdenas, C. G. EP 985651 [Chem. Abstr. 2000, 132, 207981]. For an example of bicyclization, see: (c) Muntyan, G. E.; Kurbanov, M.; Smit, V. A.; Semenovskii, A. V.; Kucherov, V. F. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 633-639 [Chem. Abstr. 1973, 79, 18869f].
11. For some references, see: (a) Schlummer, B.; Hartwig, J. F. Org. Lett. 2002, 4, 1471-1474; (b) Erman, M. B.; Hoffmann, H. M.; Cárdenas, C. G. EP 985651 [Chem. Abstr. 2000, 132, 207981]. For an example of bicyclization, see: (c) Muntyan, G. E.; Kurbanov, M.; Smit, V. A.; Semenovskii, A. V.; Kucherov, V. F. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 633-639 [Chem. Abstr. 1973, 79, 18869f].
12. For some references, see: (a) Miura, K.; Okajima, S.; Hondo, T.; Nakagawa, T.; Takahashi, T.; Hosomi, A. J. Am. Chem. Soc. 2000, 122, 11348-11357; (b) Knuebel, G.; Bomhard, A.; Market, T. DE 4439574 [Chem. Abstr. 1996, 125, 33910].
13. For some references, see: (a) Miura, K.; Okajima, S.; Hondo, T.; Nakagawa, T.; Takahashi, T.; Hosomi, A. J. Am. Chem. Soc. 2000, 122, 11348-11357; (b) Knuebel, G.; Bomhard, A.; Market, T. DE 4439574 [Chem. Abstr. 1996, 125, 33910].
14. (a) Anubhav, P. S.; Narula, A. P. S.; Schreiber, W. L. In Acid Catalyzed Reactions of Cyclic Olefinic Alcohols; Baser, K. H. C., Ed.; Flavours, fragrances and essential oils. AREP Publ.: Istanbul, 1995; pp. 78-84. For a tricyclization, see: (b) Cassel, J.; Olivero, A.; Bomhard, A. DE 4301555 [Chem. Abstr. 1994, 121, 133953].
15. (a) Anubhav, P. S.; Narula, A. P. S.; Schreiber, W. L. In Acid Catalyzed Reactions of Cyclic Olefinic Alcohols; Baser, K. H. C., Ed.; Flavours, fragrances and essential oils. AREP Publ.: Istanbul, 1995; pp. 78-84. For a tricyclization, see: (b) Cassel, J.; Olivero, A.; Bomhard, A. DE 4301555 [Chem. Abstr. 1994, 121, 133953].
16. Castro J.M., Salido S., Altarejos J., Nogueras M., Sánchez A. Tetrahedron. 58:2002;5941-5949. and references cited therein Linares, P.; Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A. In Chlorosulfonic Acid as a Cyclization Agent for Preparing Cyclic Ether Odorants; Lanzotti, V.; Taglialatela-Scafati, O., Eds.; Flavour and fragrance chemistry; Kluwer Academic Publishers: Dordrecht, 2000; pp. 101-107 and references cited therein.
17. Castro J.M., Salido S., Altarejos J., Nogueras M., Sánchez A. Tetrahedron. 58:2002;5941-5949. and references cited therein Linares, P.; Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A. In Chlorosulfonic Acid as a Cyclization Agent for Preparing Cyclic Ether Odorants; Lanzotti, V.; Taglialatela-Scafati, O., Eds.; Flavour and fragrance chemistry; Kluwer Academic Publishers: Dordrecht, 2000; pp. 101-107 and references cited therein.
18. Barrero A.F., Altarejos J., Alvarez-Manzaneda E.J., Ramos J.M., Salido S. J. Org. Chem. 61:1996;2215-2218.
19. Barrero A.F., Altarejos J., Alvarez-Manzaneda E.J., Ramos J.M., Salido S. Tetrahedron. 49:1993;6251-6262.
20. Harding, K. E.; Tiner, T. H. In Electrophilic Heteroatom Cyclizations; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Comprehensive organic synthesis, Pergamon Press: Oxford, 1991; Vol. 4, pp. 363-421.
21. Masuda, H.; Mihara, S. JP 6165879 [Chem. Abstr. 1986, 105, 97748x].
22. 2O mixture (100 mL) as eluent. This solution was concentrated to dryness, weighed and analyzed directly by GC.
23. 15.
24. Ravasio N., Leo V., Babudri F., Gargano M. Tetrahedron Lett. 38:1997;7103-7106.
25. Sugai T., Yokochi T., Watanabe N., Ohta H. Tetrahedron. 47:1991;7227-7236.
26. Whitfield F.B., Stanley G. Aust. J. Chem. 30:1977;1073-1091.
27. 18.
28. Perrin D.D., Armarego W.L.F. Purification of Laboratory Chemicals. 1988;Pergamon Press, Oxford.
29. Olah G.A., Prakash G.K.S., Sommer J. Superacids. 1985;John Wiley & Sons, New York.