Asymmetric 1,3-dipolar cycloaddition reaction between α,β- unsaturated aldehydes and nitrones catalyzed by well-defined iridium or rhodium catalysts

Advanced Synthesis and Catalysis

Volumn 349, Issue 10, 2007, Pages 1751-1758

  Carmona, Daniel ^a   Lamata, M Pilar ^a   Viguri, Fernando ^a   Rodríguez, Ricardo ^a   Fischer, Thomas ^a   Lahoz, Fernando J ^a   Dobrinovitch, Isabel T ^a   Oro, Luis A ^a  

^a CSIC UZA Instituto de Sintesis Quimica y Catalisis Homogenea ISQCH   (Spain)

Author keywords

1,3 Dipolar cycloaddition reactions; Asymmetric catalysis; Enals; Iridium; Nitrones; Rhodium

Indexed keywords

EID: 34547184971     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700010     Document Type: Article

References (35)

1. Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2002.
2. a) Synthetic applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, (Eds. : A. Padwa, W. H. Pearson), Wiley and Sons, Hoboken, New Jersey, 2003, pp 1-83;
3. b) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 867-883;
4. c) M. Frederickson, Tetrahedron 1997, 53, 403-425;
5. d) J. J. Tufariello, in: 1,3-Dipolar Cycloaddition Chemistry, (Ed.: A. Pawda), Wiley and Sons, New York, 1984, Chapter 9, pp 83-167.
6. K. V. Gothelf, K. A. Jørgensen, J. Org. Chem. 1994, 59, 5687-5691.
7. For X-ray structures of transition metal complexes containing O coordinated nitrones, see : a) J. Lee, B. Twamley, G.B. Richter-Ado, Chem. Commun. 2002, 380381;
8. b)F. A. Villamena, M. H. Dickman, D. R. Crist, Inorg. Chem. 1998, 37, 1446-1453;
9. c) D. Carmona, M. P. Lamata, F. Viguri, R. Rodríguez, L. A. Oro, F. J. Lahoz, A. I. Baiana, T. Tejero, P. Merino, J. Am. Chem. Soc. 2005, 127, 13386-13398.
10. K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458.
11. F. Viton, G. Bernardinelli, E. P. Kündig, J. Am. Chem. Soc. 2002, 124, 4968-4969.
12. a) T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Org. Lett. 2002, 4, 2457-2460;
13. b) N. Ohtsuki, S. Kezuka, Y. Kogami, T. Mita, T. Ashizawa, T. Ikeno, T. Yamada, Synthesis 2003, 1462-1466;
14. c) S. Kezuka, N. Ohtsuki, T. Mita, Y. Kogami, T. Ashizawa, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2003, 76, 2197-2207.
15. a) M. Shirahase, S. Kanemasa, Y. Oderaotoshi, Org. Lett. 2004, 6, 675-678;
16. b) M. Shirahase, S. Kanemasa, M. Hasegawa, Tetrahedron Lett. 2004, 45, 4061-4063.
17. T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 11926-11927.
18. D. Carmona, M. P. Lamata, F. Viguri, R. Rodríguez, L. A. Oro, A.I. Baiana, F.J. Lahoz, T. Tejero, P. Merino, S. Franco, I. Montesa, J. Am. Chem. Soc. 2004, 126, 2716-2717.
19. R.J. Loncharich, T. R. Schwartz, K.N. Houk, J. Am. Chem. Soc. 1987, 109, 14-23.
20. a) R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413,
21. Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
22. b) V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614,
23. Angew. Chem. Int. Ed. Engl. 1982, 21, 567-583;
24. c) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormond, J. Organomet. Chem. 1974, 73, 67-76;
25. d) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598-6599;
26. e) T. E. Sloan, Top. Stereochem. 1981, 12, 1.
27. Nomenclature of Inorganic Chemistry, (Ed.: G.J. Leigh), Blackwell, Oxford, 1991.
28. a) C. Giacovazzo, H. L. Monaco, G. Artioli, D. Viterbo, G. Ferraris, G. Gilli, G. Zanotti, M. Catti, Fundamentals of Crystallography, 2nd edn., Oxford University Press, Oxford, 2002;
29. b) D. Cremer, J. A. Pople, J. Am. Chem. Soc. 1975, 97, 1354-1358.
30. SAINT+, Software for CCD diffractometers, v. 6.01; Bruker AXS, Inc., Madison, WI, 2001 and SAINT, version 6.02.
31. R. H. Blessing, Acta Crystallogr. 1995, A51, 33-38;
32. SADABS: Area-Detector absorption correction, 1996 Bruker-AXS, Madison, WI (within SAINT+ package, v. 6.01).
33. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen, Göttingen, Germany, 1997.
34. a) H. D. Hack, Acta Crystallogr. 1983, A39, 876-881;
35. b) G. Bernardinelli, H. D. Flack, Acta Crystallogr. 1985, A41, 500-511.