One-step synthesis of chiral azamacrocycles via palladium-catalyzed enantioselective amination of 1,5-dichloroanthraquinone and 1,5- dichloroanthracene

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2299-2305

  Ranyuk, Elena R ^a   Averin, Alexei D ^a   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Amination; Enantioselectivity; Homogeneous catalysis; Macrocycles; Spontaneous resolution

Indexed keywords

EID: 77956901487     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000181     Document Type: Article

References (27)

1. a) J. M. Llinares, D. Powell, K. Bowman-James, Coord. Chem. Rev. 2003, 240, 57-75;
2. b) C. A. Ilioudis, J. W. Steed, J. Supramol. Chem. 2001, 1, 165-187;
3. c) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646;
4. R. M. Izatt, K. Pawlak, J. S. Bradshaw, Chem. Rev. 1995, 95, 2529-2586;
5. d) J. S. Bradshaw, R. M. Izatt, Acc. Chem. Res. 1997, 30, 338-345;
6. e) J. M. Lehn, Science (Washington, DC) 1985, 227, 849-856, and references cited therein.
7. a) G. Chen, Y. Xing, H. Zhang, J.-X. Gao, J. Mol. Cat. A: Chem. 2007, 273, 284-288;
8. b) J. Gao, R. A. Zingaro, J. H. Reibenspies, A. E. Martell, Org. Lett. 2004, 6, 2453-2455;
9. c) J. Gao, A. E. Martell, Org. Biomol. Chem. 2003, 1, 2795-2800;
10. d) Z. Li, C. Jablonski, Chem. Commun. 1999, 1531-1532.
11. X. X. Zhang, J. S. Bradshaw, R. M. Izatt, Chem. Rev. 1997, 97, 3313-3362.
12. S. Kobayashi, T. Hamada, S. Nagayama, K. Manabe, Org. Lett. 2001, 2, 165-167.
13. a) A. Mako, P. Bako, A. Szollosy, T. Bako, C. Peltz, P. Keglevicha, ARKIVOC 2009, vii, 165-179;
14. b) G. A. Boyle, T. Govender, H. G. Kruger, G. E. M. Maguire, Tetrahedron: Asymmetry 2004, 15, 3775-3781;
15. c) P. Bako, T. Kiss, L. Toke. Tetrahedron Lett. 1997, 38, 7259-7262;
16. d) C. Vicent, M. Martin-Lomas, S. Penades, Tetrahedron 1989, 45, 3605-3612.
17. F. Faltin, V. Fehring, R. Kadyrov, A. Arrieta, T. Schareina, R. Selke, R. Miethchen, Synthesis 2001, 4, 638-646.
18. R. M. Kellogg, Angew. Chem. 1984, 96, 769-781;
19. Angew. Chem. Int. Ed. Engl. 1984, 23, 782-794.
20. I. P. Beletskaya, A. G. Bessmertnykh, A. D. Averin, F. Denat, R. Guilard, Eur. J. Org. Chem. 2005, 281-305.
21. L. Perez-Garcia, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941-967.
22. O. Tissot, M. Gouygou, F. Dallemer, J.-C. Daran, G. G. A. Balavoine, Angew. Chem. 2001, 113, 1110-1112;
23. Angew. Chem. Int. Ed. 2001, 40, 1076-1078.
24. J. Tagashira, D. Imao, T. Yamamoto, T. Ohta, I. Furukawa, Y. Ito, Tetrahedron: Asymmetry 2005, 16, 1301-2314.
25. Copies of NMR spectra, HPLC traces and selected crystallographic data for compounds 3a, b and 5a, b are given in the Supporting Information.
26. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC 767531, CCDC 767532, and CCDC 767533. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) (+44)-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk].
27. A. D. Averin, A. N. Uglov, I. P. Beletskaya, Chem. Lett. 2008, 37, 1074-1075.