Fluorous derivatives of (1R,2R)-diaminocyclohexane as chiral ligands for metal-catalyzed asymmetric reactions

Tetrahedron Asymmetry

Volumn 16, Issue 13, 2005, Pages 2319-2327

  Bayardon, Jerome ^a   Sinou, Denis ^a   Holczknecht, Orsolya ^b   Mercs, Lászlo ^b   Pozzi, Gianluca ^b  

^a UNIVERSITÉ LYON 1   (France)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FLUORINE DERIVATIVE; LIGAND;

ARTICLE; CHEMICAL REACTION; CHIRALITY; LIGAND BINDING; PRIORITY JOURNAL; PROTON TRANSPORT; STANDARDIZATION; SUBSTITUTION REACTION;

EID: 22044443467     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.05.040     Document Type: Article

References (44)

1. Leading reviews: Y.L. Bennani, and S. Hanessian Chem. Rev. 97 1997 3161 3196
2. D. Lucet, T. Le Gall, and C. Mioskowski Angew. Chem., Int. Ed. 37 1998 2580 2627
3. F. Fache, E. Schulz, M. Tommasino, and M. Lemaire Chem. Rev. 100 2000 2159 2232
4. Selected recent examples: A. Alexakis, A. Tomassini, O. Andrey, and G. Bernardinelli Eur. J. Org. Chem. 2005 1332 1339
5. D. Xue, Y.-C. Chen, X. Cui, Q.-W. Wang, J. Zhu, and J.-G. Deng J. Org. Chem. 70 2005 3584 3591
6. H.-L. Zhang, H. Liu, X. Cui, A.-Q. Mi, Y.-Z. Jiang, and L.-Z. Gong Synlett 2005 615 618
7. D. Terakado, H. Koutaka, and T. Oriyama Tetrahedron: Asymmetry 16 2005 1157 1165
8. A.J.A. Cobb, and C.M. Marson Tetrahedron 61 2005 1269 1279
9. R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40 73 and references cited therein
10. Y.-C. Chen, T.-F. Wu, L. Jiang, J.-G. Deng, H. Liu, J. Zhu, and Y.-Z. Jiang J. Org. Chem. 70 2005 1006 1010 and references cited therein
11. A. Brethon, J.J.E. Moreau, and M. Wong Chi Man Tetrahedron: Asymmetry 15 2004 495 502 and references cited therein
12. D.E. De Vos I.F.J. Vankelecom P.A. Jacobs Chiral Catalyst Immobilization and Recycling 2000 Wiley-VCH Weinheim
13. Q.-H. Fan, Y.-M. Li, and A.S.C. Chan Chem. Rev. 102 2002 3385 3466
14. P.N. Liu, P.N. Gu, F. Wang, and Y.Q. Tu Org. Lett. 6 2004 169 172
15. X. Li, W. Chen, W. Hems, F. King, and J. Xiao Org. Lett. 5 2003 4559 4561
16. X. Li, W. Chen, W. Hems, F. King, and J. Xiao Tetrahedron Lett. 45 2004 951 953
17. S. Itsuno, A. Tsuji, and M. Takahashi Tetrahedron Lett. 44 2003 3825 3828
18. S. Itsuno, M. Takahashi, and A. Tsuji Macromol. Symp. 217 2004 191 202
19. A. Ferrand, M. Bruno, M.L. Tommasino, and M. Lemaire Tetrahedron: Asymmetry 13 2002 1379 1384
20. C. Maillet, T. Praveen, P. Janvier, S. Minguet, M. Evain, C. Saluzzo, M.L. Tommasino, and B. Bujoli J. Org. Chem. 67 2002 8191 8196
21. Y. Ma, H. Liu, L. Chen, X. Cui, J. Zhu, and J. Deng Org. Lett. 5 2003 2103 2106
22. Reviews: G. Pozzi, and I. Shepperson Coord. Chem. Rev. 242 2003 115 124
23. D. Sinou Enantioselective Catalysis: Biphasic Conditions J.A. Gladysz D. Curran I.T. Horváth Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim 306 315
24. S. Takeuchi, and Y. Nakamura Enantioselective Catalysis in Non-Biphasic Conditions J.A. Gladysz D. Curran I.T. Horváth Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim 316 322
25. F. Fache New J. Chem. 2004 1277 1283
26. D. Maillard, G. Pozzi, S. Quici, and D. Sinou Tetrahedron 58 2002 3971 3976
27. I. Shepperson, S. Quici, G. Pozzi, M. Nicoletti, and D. O'Hagan Eur. J. Org. Chem. 2004 4545 4551
28. J. Bayardon, and D. Sinou Synthesis 2005 425 428
29. G. Pozzi, S. Quici, and I. Shepperson Tetrahedron Lett. 43 2002 6141 6143 and references cited therein
30. F. De Campo, D. Lastécouères, J.-M. Vincent, and J.-B. Verlhac J. Org. Chem. 64 1999 4969 4971
31. O. Holczknecht, M. Cavazzini, S. Quici, I. Shepperson, and G. Pozzi Adv. Synth. Catal. 347 2005 677 688
32. A. Alexakis, A.-S. Chauvin, R. Stounevel, E. Vrancken, S. Mutti, and P. Mangeney Tetrahedron: Asymmetry 12 2001 1171 1178
33. J. Rábai Getting Started in Synthesis: A Tabular Guide to Selected Monofunctional Fluorous Compounds J.A. Gladysz D. Curran I.T. Horváth Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim 156 174
34. S. Achilefu, L. Mansuy, C. Selve, and S. Thiebaut J. Fluorine Chem. 70 1995 19 26
35. D. Tra Anh, H. Blancou, and A. Commeyras J. Fluorine Chem. 96 1999 167 174
36. J. Bayardon, D. Maillard, G. Pozzi, and D. Sinou Tetrahedron: Asymmetry 15 2004 2633 2640
37. K. Fuji, H. Ohnishi, S. Moriyama, K. Tanaka, T. Kawabata, and K. Tsubaki Synlett 2000 351 352
38. J. Bayardon, and D. Sinou J. Org. Chem. 69 2004 3121 3128
39. J. Bayardon, M. Cavazzini, D. Maillard, G. Pozzi, S. Quici, and D. Sinou Tetrahedron: Asymmetry 14 2003 2215 2224
40. T. Katsuki Metal Complexes as Catalysts for Oxygen, Nitrogen, and Carbon-atom Transfer Reactions J.A. McCleverty T.J. Meyer Comprehensive Coordination Chemistry II 2004 Elsevier Oxford 207 264
41. S. Kanemasa, S. Hamura, E. Harada, and H. Yamamoto Tetrahedron Lett. 35 1994 7985 7988
42. C. Borriello, M.E. Cucciolito, A. Panunzi, and F. Ruffo Tetrahedron: Asymmetry 12 2001 2467 2471
43. B. Hungerhoff, H. Sonnenschein, and F. Theil J. Org. Chem. 67 2002 1781 1785
44. J.M. Vincent, A. Rabion, V.K. Yachandra, and R.H. Fish Can. J. Chem. 79 2001 888 895