Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

Tetrahedron Letters

Volumn 46, Issue 45, 2005, Pages 7747-7750

  Anderson, Erin D ^a   Ernat, Justin J ^a   Nguyen, Mai P ^a   Palma, Ann C ^a   Mohan, Ram S ^a  

^a ILLINOIS WESLEYAN UNIVERSITY   (United States)

Author keywords

Bismuth and compounds; Carbonyl ene reaction; Cyclizations; Lewis acids

Indexed keywords

ALDEHYDE; BISMUTH DERIVATIVE; BISMUTH TRIFLATE; CARBONYL DERIVATIVE; CITRONELLAL; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; METHODOLOGY; SYNTHESIS;

EID: 26444524950     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.035     Document Type: Article

References (30)

1. W. Oppolzer, and V. Snieckus Angew. Chem., Int. Ed. Engl. 17 1978 476
2. B.B. Snider Acc. Chem. Res. 13 1980 426
3. K. Mikami, and M. Shimizu Chem. Rev. 92 1992 1021
4. M. Trost Barry Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Press 527
5. Y. Nakatani, and K. Kawashima Synthesis 1978 147
6. V.K. Aggarwal, G.P. Vennall, P.N. Davey, and C. NewMan Tetrahedron Lett. 39 1998 1997
7. P. Kocovsky, G. Ahmed, J. Srogl, A.V. Malkov, and J. Steele J. Org. Chem. 64 1999 2765
8. G.K. Chuah, S.H. Liu, S. Jaenicke, and L.J. Harrison J. Catal. 200 2001 352
9. C.K. Andrade, O.E. Vercillo, J.P. Rodrigues, and D.P. Silveira J. Braz. Soc. 15 2004 813
10. K.A. da Silva, P.A. Robles-Dutenhefner, E.M.B. Sousa, E.F. Kozhevnikova, I.V. Kozhevnikov, and E.V. Gusevskaya Catal. Commun. 5 2004 425
11. J. Reglinski N.C. Norman Chemistry of Arsenic, Antimony and Bismuth 1998 Blackie Academic and Professional New York 403 440
12. H. Suzuki Y. Matano Organobismuth Chemistry 2001 Elsevier Amsterdam
13. For recent reviews on use of bismuth(III) compounds in organic synthesis see: N.M. Leonard, L.C. Wieland, and R.S. Mohan Tetrahedron 58 2002 8373
14. H. Gaspard-Iloughmane, and C. Le Roux Eur. J. Org. Chem. 2004 2517
15. 3 as a catalyst in organic synthesis, see: P.A. Anzalone, A.R. Baru, E.M. Danielson, P.D. Hayes, M.P. Nguyen, A.F. Panico, R.C. Smith, and R.S. Mohan J. Org. Chem. 70 2005 2091
16. B. Sreedhar, V. Swapna, Ch. Sridhar, D. Saileela, and A. Sunitha Synth. Commun. 35 2005 1177
17. B. Sreedhar, V. Swapna, and Ch. Sridhar Catal. Commun. 6 2005 293
18. M. Khodaei, A.R. Khosorpur, and M. Kookhazadeh Can. J. Chem. 83 2005 209
19. J.S. Yadav, B.V.S. Reddy, T. Swamy, and R.K. Rao Tetrahedron Lett. 45 2004 6037
20. J.S. Yadav, B.V.S. Reddy, and K. Premalatha Synlett 2004 963
21. Y. Matsushita, K. Sugamoto, and T. Matsui Tetrahedron Lett. 45 2004 4723
22. T. Ollevier, and G. Lavie-Compin Tetrahedron Lett. 45 2004 49
23. J.N. Arnold, P.D. Hayes, R.L. Kohaus, and R.S. Mohan Tetrahedron Lett. 44 2003 9173
24. Bismuth triflate was purchased from Lancaster Chemical Company. It can also be synthesized in the laboratory from triphenylbismuth and triflic acid, see: M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, J. Dubac, and J.R. Desmurs Tetrahedron Lett. 40 1999 285
25. Recently, a synthesis of bismuth triflate from bismuth oxide and triflic acid in aqueous ethanol has been reported. S. Répichet, A. Zwick, L. Vendier, C. Le Roux, and J. Dubac Tetrahedron Lett. 43 2002 993
26. A more convenient procedure for the synthesis of bismuth triflate uses chlorobenzene as the solvent, see: S.M. Peyronneau, C. Arrondo, L. Vendier, N. Roques, and C. Le Roux J. Mol. Catal. A 211 2004 89
27. L. Peidro, C. Le Roux, A. Laporterie, and J. Dubac J. Organomet. Chem. 521 1996 397 Although the authors do not report the ratio of the diastereomeric products obtained from cyclization of citronellal, isopulegol is reported to be the major product (70%)
28. J.T. Williams, P.S. Bahia, and J.S. Snaith Org. Lett. 4 2002 21
29. 13C NMR spectroscopy and GC as well as by comparison of their spectra with those of authentic samples.
30. 12.