Allylic amination by a DNA-diene-iridium(I) hybrid catalyst

Angewandte Chemie - International Edition

Volumn 48, Issue 24, 2009, Pages 4426-4429

  Fournier, Pierre ^a   Fiammengo, Roberto ^a   Jäschke, Andres ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Allylic substitution; Diene ligands; DNA; Hybrid catalysis; Iridium

Indexed keywords

ALLYLIC AMINATION; ALLYLIC SUBSTITUTION; AQUEOUS MEDIUM; DIENE LIGANDS; DNA STRANDS; FUNCTIONALIZED; HIGH STABILITY; HYBRID CATALYSIS; HYBRID CATALYSTS; SECONDARY STRUCTURES;

AMINATION; AMINES; CATALYSIS; DNA; IRIDIUM; IRIDIUM COMPOUNDS; LIGANDS; NUCLEIC ACIDS; OLEFINS; ORGANOMETALLICS; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

GENES;

DNA; IRIDIUM; OLIGONUCLEOTIDE; POLYENE;

AMINATION; CATALYSIS; CHEMISTRY; KINETICS; STEREOISOMERISM;

AMINATION; CATALYSIS; DNA; IRIDIUM; KINETICS; OLIGONUCLEOTIDES; POLYENES; STEREOISOMERISM;

EID: 70349975681     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900713     Document Type: Article

References (33)

1. a) J. Steinreiber, T. R. Ward, Coord. Chem. Rev. 2008, 252, 751-766;
2. b) M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1978, 100, 306-307;
3. c) M.T. Reetz, M. Rentzsch, A. Pletsch, M. Maywald, P. Maiwald, J.J. P. Peyralans, A. Maichele, Y. Fu, N. Jiao, F. Hollmann, R. Mondiere, A. Taglieber, Tetrahedron 2007, 63, 6404-6414;
4. d) A. Pordea, M. Creus, J. Panek, C. Duboc, D. Mathis, M. Novic, T. R. Ward, J. Am. Chem. Soc. 2008, 130, 8085-8088;
5. e) J. Pierron, C. Malan, M. Creus, J. Gradinaru, J. Hafner, A. Ivanova, A. Sardo, T. R. Ward, Angew. Chem. 2008, 120, 713-717;
6. Angew. Chem. Int. Ed. 2008, 47, 701-705.
7. a) G. Roelfes, B. L. Feringa, Angew. Chem. 2005, 117, 3294-3296;
8. Angew. Chem. Int. Ed. 2005, 44, 3230-3232;
9. b) N. S. Oltra, G. Roelfes, Chem. Commun. 2008, 6039-6041;
10. c) D. Coquière, B. L. Feringa, G. Roelfes, Angew. Chem. 2007, 119, 9468-9471;
11. Angew. Chem. Int. Ed. 2007, 46, 9308-9311;
12. d) N. Shibata, H. Yasui, S. Nakamura, T. Toru, Synlett 2007, 1153-1157;
13. e) U. Jakobsen, K. Rohr, S. Vogel, Nucleosides Nucleotides Nucleic Acids 2007, 26, 1419-1422.
14. a) C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558-4579;
15. Angew. Chem. Int. Ed. 2008, 47, 4482-4502;
16. b) T. Gendrineau, O. Chuzel, H. Eijsberg, J.-R Genet, S. Darses, Angew. Chem. 2008, 120, 7783-7786;
17. Angew. Chem. Int. Ed. 2008, 47, 7669-7672;
18. c) T. Nishimura, Y. Yasuhara, M. Nagaosa, T. Hayashi, Tetrahedron: Asymmetry 2008, 19, 1778-1783;
19. d) K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett. 2008, 10, 4387-4389.
20. C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628-1629.
21. Y. Z. Xu, Q. Zheng, R. F. Swann, J. Org. Chem. 1992, 57, 3839-3845.
22. M. Caprioara, R. Fiammengo, M. Engeser, A. Jäschke, Chem. Eur. J. 2007, 13, 2089-2095.
23. For Ll, L2, and L3, (SRR) is (1S,4R, 8R) and (RSS) is (lR,4S,8S).
24. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675-691.
25. As is common for iridium-catalyzed allylic substitution, the reaction gave rise to the branched product only.
26. a) D. Sinou, C. Rabeyrin, C. Nguefack, Adv. Synth. Catal. 2003, 345, 357-363;
27. b) C. Chevrin, J. Le Bras, F. Henin, J. Muzart, A. Pla-Quintana, A. Roglans, R. Pleixats, Organometallics 2004, 23, 4796-4799;
28. c) H. Kinoshita, H. Shinokubo, K. Oshima, Org. Lett. 2004, 6, 4085-4088.
29. The reactions went to near completion despite acidification of the medium upon liberation of acetic acid.
30. The stereoselectivity factor was estimated from the ee value of remaining starting material according to: H. B. Kagan, J. C. Fiaud, Top. Curr. Stereochem. 1988, 18, 249-330.
31. a) G. F. Joyce, Angew. Chem. 2007, 119, 6540-6557;
32. Angew. Chem. Int. Ed. 2007, 46, 6420-6436;
33. b) M. T. Reetz, Proc. Natl. Acad. Sci. USA 2004, 101, 5716-5722.