Ether-directed palladium(II)-catalysed aza-Claisen rearrangements: studies on the origin of the directing effect

Tetrahedron

Volumn 63, Issue 10, 2007, Pages 2123-2131

  Jamieson, Andrew G ^a   Sutherland, Andrew ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Aza Claisen rearrangement; Directing effect; Palladium catalysis

Indexed keywords

ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; OXYGEN; PALLADIUM; TRICHLOROACETIMIDIC ACID;

ARTICLE; CATALYST; CLAISEN REARRANGEMENT; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33846627635     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.067     Document Type: Article

References (45)

1. Overman L.E., and Carpenter N.E. Org. React. 66 (2005) 1 and references therein
2. For recent examples see:
3. Reilly M., Anthony D.R., and Gallagher C. Tetrahedron Lett. 44 (2003) 2927
4. Lurain A.E., and Walsh P.J. J. Am. Chem. Soc. 125 (2003) 10677
5. Kim S., Lee T., Lee E., Lee J., Fan G.-J., Lee S.K., and Kim D. J. Org. Chem. 69 (2004) 3144
6. Jamieson A.G., Sutherland A., and Willis C.L. Org. Biomol. Chem. 2 (2004) 808
7. Overman L.E. J. Am. Chem. Soc. 98 (1976) 2901
8. Overman L.E. Angew. Chem., Int. Ed. Engl. 23 (1984) 579
9. Schenck T.G., and Bosnich B. J. Am. Chem. Soc. 107 (1985) 2058
10. Fanning K.N., Jamieson A.G., and Sutherland A. Curr. Org. Chem. 10 (2006) 1007
11. Calter M., Hollis T.K., Overman L.E., Ziller J., and Zipp G.G. J. Org. Chem. 62 (1997) 1449
12. Hollis T.K., and Overman L.E. Tetrahedron Lett. 38 (1997) 8837
13. Uozumi Y., Kato K., and Hayashi T. Tetrahedron: Asymmetry 9 (1998) 1065
14. Kang J., Kim T.H., Yew K.H., and Lee W.K. Tetrahedron: Asymmetry 14 (2003) 415
15. Overman L.E., Owen C.E., Pavan M.M., and Richards C.J. Org. Lett. 5 (2003) 1809
16. Anderson C.E., and Overman L.E. J. Am. Chem. Soc. 125 (2003) 12412
17. Kirsch S.F., Overman L.E., and Watson M.P. J. Org. Chem. 69 (2004) 8101
18. Anderson C.E., Donde Y., Douglas C.J., and Overman L.E. J. Org. Chem. 70 (2005) 648
19. Jamieson A.G., and Sutherland A. Org. Biomol. Chem. 3 (2005) 735
20. Jamieson A.G., and Sutherland A. Org. Biomol. Chem. 4 (2006) 2932
21. Yoon Y.-J., Chun M.-H., Joo J.-E., Kim Y.-H., Oh C.-Y., Lee K.-Y., Lee Y.-S., and Ham W.-H. Arch. Pharm. Res. 27 (2004) 136
22. Fanning K.N., Jamieson A.G., and Sutherland A. Org. Biomol. Chem. 3 (2005) 3749
23. Swift M.D., and Sutherland A. Org. Biomol. Chem. 4 (2006) 3889
24. Ireland R.E., and Norbeck D.W. J. Org. Chem. 50 (1985) 2198
25. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., and Sakai T. Tetrahedron Lett. 25 (1984) 2183
26. Sutherland A., and Willis C.L. Bioorg. Med. Chem. Lett. 9 (1999) 1941
27. Myers A.G., Yang B.H., Chen H., McKinstry L., Kopecky D.J., and Gleason J.L. J. Am. Chem. Soc. 119 (1997) 6496
28. As previously reported in Ref. 8a, the relative stereochemistry of the rearrangement products was determined by conversion of the allylic trichloroamides into the corresponding oxazolidin-2-ones. Using NOE experiments then allowed assignment of the major diastereomer. More recently (Ref. 10a), the conversion of the allylic amides into known β-hydroxy-α-amino acids has further confirmed this original assignment.
29. 1H NMR spectra produced from rearrangement of the carbon analogue and allylic amide 10 allowed confirmation of diastereomer b as the major product from these reactions.
30. Nitrogen directed Overman rearrangements have also been observed:. Gonda J., Helland A.-C., Ernst B., and Bellus D. Synthesis (1993) 729
31. Corey E.J., and Bock M.G. Tetrahedron Lett. 16 (1975) 3269
32. Holton R.A., and Davis R.G. Tetrahedron Lett. 18 (1977) 533
33. Yamda K., Kato K., Nagase H., and Hirata Y. Tetrahedron Lett. 17 (1976) 65
34. Suzuki K., Inanaga J., and Yamaguchi M. Chem. Lett. (1979) 1277
35. Jaunzeme I., and Jirgensons A. Synlett (2005) 2984
36. Birch A.J., and Walker K.A.M. Tetrahedron Lett. 8 (1967) 1935
37. Barbier J., Lamy-Pitara E., Marecot P., Boitiaux J.P., Cosyns J., and Verna F. Adv. Catal. 37 (1990) 279
38. Mayer S.C., Ramanjulu J., Vera M.D., Pfizenmayer A.J., and Joullie M.M. J. Org. Chem. 59 (1994) 5192
39. Philli R.A., Victor M.M., and de Meijere A. J. Org. Chem. 65 (2000) 5910
40. Annuziata R., Conquini M., Cozzi F., Dondis G., and Raimondi L. Tetrahedron 43 (1987) 2369
41. Lattanzi A., Sagulo F., and Scettri A. Tetrahedron: Asymmetry 10 (1999) 2023
42. Broggini G., Molteni G., and Pilati T. Tetrahedron: Asymmetry 11 (2000) 1975
43. El-Abadelah M.M. Tetrahedron 29 (1973) 589
44. Loseva M., Chernova N., Vorflusev V., Beresnev L., Hiller S., and Hasse W. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 260 (1995) 261
45. Sheehan M., Spangler R.J., Ikeda M., and Djerassi C. J. Org. Chem. 36 (1971) 1796