The first one-pot Alder-ene-reductive amination sequence

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2155-2158

  Kressierer, Christoph J ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Amination; Catalysis; Domino reactions; Ene reactions

Indexed keywords

ACETALDEHYDE; ALLYL ALCOHOL; AMINE; FORMIC ACID; PALLADIUM; TETRAHYDROFURAN DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ISOMERIZATION; ONE POT REACTION; REDUCTION;

BETULACEAE;

EID: 1242340494     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.033     Document Type: Article

References (31)

1. Ugi I., Dömling A., Werner B. J. Heterocycl. Chem. 37:2000;647-658.
2. Posner G.H. Chem. Rev. 86:1986;831-844.
3. Weber L., Illgen K., Almstetter M. Synlett. 1999;366-374.
4. Kobayashi S. Chem. Soc. Rev. 28:1999;1-15.
5. For recent excellent reviews on transition metal assisted sequential transformations and domino processes, see for example: Balme G., Bossharth E., Monteiro N. Eur. J. Org. Chem. 2003;4101-4111.
6. Battistuzzi G., Cacchi S., Fabrizi G. Eur. J. Org. Chem. 2002;2671-2681.
7. Negishi E.-I., Copéret C., Ma S., Liou S.-Y., Liu F. Chem. Rev. 96:1996;365-393.
8. Tietze L.F. Chem. Rev. 96:1996;115-136.
9. For representative transition metal catalyzed Alder-ene reactions, see for example, Pd: Trost B.M. Acc. Chem. Res. 23:1990;34-42.
10. Trost B.M. Janssen Chim. Acta. 9:1991;3-9.
11. Trost B.M., Krische M.J. Synlett. 1998;1-16.
12. Ru: Trost B.M. Chem. Ber. 129:1996;1313-1322.
13. Trost B.M., Toste F.D. Tetrahedron Lett. 40:1999;7739-7743.
14. Rh: Cao P., Wang B., Zhang X. J. Am. Chem. Soc. 122:2000;6490-6491.
15. Cao P., Zhang X. Angew. Chem. 112:2000;4270-4272.
16. Lei A., He M., Zhang X. J. Am. Chem. Soc. 124:2002;8198-8199.
17. Ir: Chatani N., Inoue H., Morimoto T., Muto T., Murai S. J. Org. Chem. 66:2001;4433-4436.
18. Ti: Sturla S.J., Kablaoui N.M., Buchwald S.L. J. Am. Chem. Soc. 121:1999;1976-1977.
19. Karpov A.S., Müller T.J.J. Org. Lett. 5:2003;3451-3454.
20. Karpov A.S., Rominger F., Müller T.J.J. J. Org. Chem. 68:2003;1503-1511.
21. Braun R.U., Zeitler K., Müller T.J.J. Org. Lett. 3:2001;3297-3300.
22. Müller T.J.J., Robert J.P., Schmälzlin E., Bräuchle C., Meerholz K. Org. Lett. 2:2000;2419-2422.
23. Müller T.J.J., Ansorge M., Aktah D. Angew. Chem., Int. Ed. 39:2000;1253-1256.
24. Trost B.M., Li Y. J. Am. Chem. Soc. 118:1996;6625-6633.
25. Yamada H., Aoyagi S., Kibayashi C. Tetrahedron Lett. 38:1997;3027-3030.
26. The synthesis of yne allyl alcohol substrates were performed according to Sajiki H., Hirota K. Tetrahedron. 54:1998;13981-13996. The detailed protocols will be described elsewhere.
27. 2Si (198.3): C, 60.56; H, 9.15. Found: C, 60.04; H, 9.02.
28. All compounds have been fully characterized spectroscopically and by correct elemental analysis or HRMS, respectively.
29. For reviews, see for example: Moore M.L. Org. React. 5:1949;301-330.
30. Lukasiewicz A. Tetrahedron. 19:1963;1789-1799.
31. 31NOSi (281.5): C, 68.27; H, 11.10; N, 4.98. Found: C, 68.00; H, 10.97; N, 4.92.