From terminal alkynes directly to branched amines

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3217-3221

  Garcia Castro, Ivette ^a   Tillack, Annegret ^a   Hartung, Christian G ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; ALKYNE; AMINE; ORGANOLITHIUM COMPOUND;

AMINATION; ARTICLE; SYNTHESIS;

EID: 0037424752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00448-9     Document Type: Article

References (34)

1. Collin D.T., Hartley D., Jack D., Lunts L.H.C., Press J.C., Ritchie A.C., Toon P. J. Med. Chem. 13:1970;674-680.
2. Aoyagi S., Tanaka R., Naruse M., Kibayashi C. Tetrahedron Lett. 39:1998;4513-4516.
3. Palacios M., Aparicio D., Garcia J. Tetrahedron. 52:1996;9609-9628.
4. Klusener P.A.A., Tip L., Brandsma L. Tetrahedron. 47:1991;2041-2064.
5. Cliffe I.A., Crossley R., Sheferd R.G. Synthesis. 1985;1138-1140.
6. Fetell A.I., Feuer H. J. Org. Chem. 43:1978;497-500.
7. Layer R.W. Chem. Rev. 63:1963;489-510.
8. Texier-Boullet F. Synthesis. 1985;679-681.
9. Kyba E. Org. Prep. Proc. 2:1970;149.
10. Feringa B.L., Jansen J.F.G.A. Synthesis. 1988;184-186.
11. Saidi M.R., Azizi N., Zali-Boinee H. Tetrahedron. 57:2001;6829-6832.
12. For reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Haak, E.; Doye, S. Chem. unserer Zeit 1999, 33, 297-303; (c) Nobis, M.; Drießen-Hölscher, B. Angew. Chem. 2001, 113, 4105-4108; Angew. Chem., Int. Ed. 2001, 40, 3983-3986. For a personal account, see: (d) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
13. For reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Haak, E.; Doye, S. Chem. unserer Zeit 1999, 33, 297-303; (c) Nobis, M.; Drießen-Hölscher, B. Angew. Chem. 2001, 113, 4105-4108; Angew. Chem., Int. Ed. 2001, 40, 3983-3986. For a personal account, see: (d) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
14. For reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Haak, E.; Doye, S. Chem. unserer Zeit 1999, 33, 297-303; (c) Nobis, M.; Drießen-Hölscher, B. Angew. Chem. 2001, 113, 4105-4108; Angew. Chem., Int. Ed. 2001, 40, 3983-3986. For a personal account, see: (d) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
15. For reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Haak, E.; Doye, S. Chem. unserer Zeit 1999, 33, 297-303; (c) Nobis, M.; Drießen-Hölscher, B. Angew. Chem. 2001, 113, 4105-4108; Angew. Chem., Int. Ed. 2001, 40, 3983-3986. For a personal account, see: (d) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
16. For reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Haak, E.; Doye, S. Chem. unserer Zeit 1999, 33, 297-303; (c) Nobis, M.; Drießen-Hölscher, B. Angew. Chem. 2001, 113, 4105-4108; Angew. Chem., Int. Ed. 2001, 40, 3983-3986. For a personal account, see: (d) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
17. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
18. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
19. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
20. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
21. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
22. For recent examples, see: (a) Johnson, J. S.; Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923-2924; (b) Pohlki, F.; Doye, S. Angew. Chem. 2001, 113, 2361-2364; Angew. Chem., Int. Ed. 2001, 40, 2305-2308; (c) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011-5013, (d) Pohlki, F.; Heutling, A.; Bytschkov, I.; Hotopp, T.; Doye, S. Synlett 2002, 799-801, (e) Ong, T.-G.; Yap, G. P. A.; Richeson, D. S. Organometallics 2002, 21, 2839-2841.
23. Hartung C.G., Tillack A., Trauthwein H., Beller M. J. Org. Chem. 66:2001;6339-6343 Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem. 1999, 111, 3416-3419; Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
24. Hartung C.G., Tillack A., Trauthwein H., Beller M. J. Org. Chem. 66:2001;6339-6343 Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem. 1999, 111, 3416-3419; Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
25. Hartung C.G., Tillack A., Trauthwein H., Beller M. J. Org. Chem. 66:2001;6339-6343 Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem. 1999, 111, 3416-3419; Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
26. Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem. Int. Ed. 2002, 41, 2541-2543; Angew. Chem. 2002, 114, 2646-2648.
27. Tillack, A.; Garcia Castro, I.; Hartung, C. G.; Beller, M. Angew. Chem. Int. Ed. 2002, 41, 2541-2543; Angew. Chem. 2002, 114, 2646-2648.
28. Burlakov V.V., Rosenthal U., Petrovskii P.V., Shur V.B., Vol'pin M.E. Organomet. Chem. USSR. 1:1988;526.
29. Tillack A., Lefeber C., Peulecke N., Thomas D., Rosenthal U. Tetrahedron Lett. 38:1997;1533-1534 Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal, U. Angew. Chem. 1998, 110, 2029-2031; Angew. Chem., Int. Ed. 1998, 37, 1915-1927 Arndt, P.; Spannenberg, A.; Baumann, W.; Becke, S.; Rosenthal, U. Eur. J. Inorg. Chem. 2001, 2885-2890; Rosenthal's catalysts is commercially available from Fluka.
30. Tillack A., Lefeber C., Peulecke N., Thomas D., Rosenthal U. Tetrahedron Lett. 38:1997;1533-1534 Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal, U. Angew. Chem. 1998, 110, 2029-2031; Angew. Chem., Int. Ed. 1998, 37, 1915-1927 Arndt, P.; Spannenberg, A.; Baumann, W.; Becke, S.; Rosenthal, U. Eur. J. Inorg. Chem. 2001, 2885-2890; Rosenthal's catalysts is commercially available from Fluka.
31. Tillack A., Lefeber C., Peulecke N., Thomas D., Rosenthal U. Tetrahedron Lett. 38:1997;1533-1534 Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal, U. Angew. Chem. 1998, 110, 2029-2031; Angew. Chem., Int. Ed. 1998, 37, 1915-1927 Arndt, P.; Spannenberg, A.; Baumann, W.; Becke, S.; Rosenthal, U. Eur. J. Inorg. Chem. 2001, 2885-2890; Rosenthal's catalysts is commercially available from Fluka.
32. Tillack A., Lefeber C., Peulecke N., Thomas D., Rosenthal U. Tetrahedron Lett. 38:1997;1533-1534 Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal, U. Angew. Chem. 1998, 110, 2029-2031; Angew. Chem., Int. Ed. 1998, 37, 1915-1927 Arndt, P.; Spannenberg, A.; Baumann, W.; Becke, S.; Rosenthal, U. Eur. J. Inorg. Chem. 2001, 2885-2890; Rosenthal's catalysts is commercially available from Fluka.
33. Martelli G., Morri S., Savoia D. Tetrahedron. 56:2000;8367-8374.
34. +). All compounds are new and were characterized by NMR, MS, and IR.