I--catalyzed reaction of 5-methoxyoxazoles with organic iodides - An efficient synthesis of azalactones

European Journal of Organic Chemistry

Volumn , Issue 4, 2007, Pages 676-680

  Lu, Lianghua ^a   Lu, Ping ^a   Shengming, Ma ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Azalactones; Cleavage reactions; Heterocycles; Organic iodides; Oxazoles

Indexed keywords

EID: 33846644056     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600637     Document Type: Article

References (23)

1. a) P. A. Bartlett, J. F. Barstow, J. Org. Chem. 1982, 47, 3933-3941;
2. b) K. Burger, K. Gaa, K. Geith, C. Schierlinger, Synthesis 1989, 850-855;
3. c) S. A. Shaw, P. Aleman, E. Vedejs, J. Am. Chem. Soc. 2003, 125, 13368-13369.
4. a) W. Steglich, G. Höfle, Tetrahedron Lett. 1970, 11, 4727-4730;
5. b) J. C. Ruble, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 11532-11533;
6. c) J. G. Seitzberg, C. Dissing, I. Søtofte, P.-O. Norrby, M. Johannsen, J. Org. Chem. 2005, 70, 8332-8337;
7. d) S. A. Shaw, P. Aleman, J. Christy, J. W. Kampf, P. Va, E. Vedejs, J. Am. Chem. Soc. 2006, 128, 925-934.
8. S. Ma, L. Lu, P. Lu, J. Org. Chem. 2005, 70, 1063-1065.
9. D. Obrecht, M. Altorfer, C. Lehmann, P. Schönholzer, K. Müller, J. Org. Chem. 1996, 61, 4080-4086.
10. D. Obrecht, U. Bohdal, C. Broger, D. Bur, C. Lehmann, R. Ruffieux, P. Schönholzer, C. Sepielger, K. Müller, Helv. Chim. Acta 1995, 78, 563-580.
11. Y. S. Rao, R. Filler in The Chemistry of Heterocyclic Compounds - A Series of Monographs: Oxazolones (Eds.: A. Weissberger, E. C. Taylor), Wiley, New York, 1986, pp. 363-691.
12. a) T. Wirth, Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227 and references cited therein;
13. b) A. K. Mukerjee, Heterocycles 1987, 26, 1077-1097;
14. c) P. Lloyd-Williams, N. Carulla, E. Giralt, Tetrahedron Lett. 1997, 38, 299-302;
15. d) B. M. Trost, C. Lee, J. Am. Chem. Soc. 2001, 123, 12191-12201.
16. a) B. M. Trost, X. Ariza, J. Am. Chem. Soc. 1999, 121, 10727-10737;
17. b) B. M. Trost, K. Dogra, J. Am. Chem. Soc. 2002, 124, 7256-7257;
18. c) B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439;
19. d) X. Liu, J. F. Hartwig, Org. Lett. 2003, 5, 1915-1918.
20. A. Avenoza, J. H. Busto, C. Cativiela, J. M. Peregrina, Tetrahedron Lett. 2002, 43, 4167-4170.
21. R. Connell, F. Scavo, P. Helquit, B. Akermark, Tetrahedron Lett. 1986, 27, 5559-5562.
22. int = 0.0665), parameters 220. CCDC-610577 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
23. L. P. Hadjiarapoglu, Tetrahedron Lett. 2002, 43, 5997-6000.