Synthesis of new mono-N-tosylated diamine ligands based on (R)-(+)-limonene and their application in asymmetric transfer hydrogenation of ketones and imines

Tetrahedron Asymmetry

Volumn 24, Issue 11, 2013, Pages 643-650

  Roszkowski, Piotr ^a   Maurin, Jan K ^b,c   Czarnocki, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b NATIONAL MEDICINES INSTITUTE   (Poland)

^c NATIONAL CENTRE FOR NUCLEAR RESEARCH   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; DIAMINE DERIVATIVE; IMINE; KETONE DERIVATIVE; LIGAND; LIMONENE; RUTHENIUM DERIVATIVE; SODIUM AZIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL INTERACTION; CHIRALITY; DRUG STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 84878566399     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.04.010     Document Type: Article

References (43)

1. B.A. Pawson, H-C. Cheung, S. Gurbaxani, and G. Saucy J. Am. Chem. Soc. 92 1970 336 343
2. E.E. Van Tamelen, and R.J. Anderson J. Am. Chem. Soc. 94 1972 8225 8228
3. K. Mori, and M. Kato Tetrahedron 42 1986 5895 5900
4. B.E. Marron, and K.C. Nicolaou Synthesis 1989 537 540
5. M.A. Tius, and M.A. Kerr Synth. Commun. 18 1988 1905 1911
6. R. Baudouy, and P. Prince Tetrahedron 45 1989 2067 2074
7. L.A. Paquette, and H-J. Kang J. Am. Chem. Soc. 113 1991 2610 2621
8. C.T. Goralski, W. Chrisman, D.L. Hasha, L.W. Nicholson, P.R. Rudolf, D. Zakett, and B. Singaram Tetrahedron: Asymmetry 8 1997 3863 3871
9. D. Steiner, S.G. Sethofer, C.T. Goralski, and B. Singaram Tetrahedron: Asymmetry 13 2002 1477 1483
10. M. Masui, and T. Shioiri Tetrahedron 51 1995 8363 8370
11. G.S. Kauffman, G.D. Harris, L.R. Dorow, B.R.P. Stone, R.L. Parsons Jr., J.A. Pesti, N.A. Magnus, J.M. Fortunak, P.N. Confalone, and W.A. Nugent Org. Lett. 2 2000 3119 3121
12. Y.L. Bennani, and S. Hanessian Chem. Rev. 97 1997 3161 3195
13. S.V. Larionov, A.V. Tkachev, L.I. Myachina, Z.A. Savel'eva, L.A. Glinskaya, R.F. Klevtsova, A.M. Agafontsev, and S.N. Bizyaev Russ. J. Coord. Chem. 35 2009 286 295
14. C.M. Binder, A. Bautista, M. Zaidlewicz, M.P. Krzemiński, A. Olivier, and B. Singaram J. Org. Chem. 74 2009 2337 2343
15. B.D. Mookherjee, and RA. Wilson 4th ed. Kirk-Othmer Encyclopedia of Chemical Technology Vol. 17 1996 John Wiley & Sons New York 603 674
16. R.M. Carman, and K.D. Klika Aust. J. Chem. 44 1991 1803 1808
17. J. Cubillos, S. Vásquez, and C.M. de Correra Appl. Catal. A: Gen. 373 2010 57 65
18. C.C. Watts, P. Thoniyot, l.C. Hirayama, T. Romano, and B. Singaram Tetrahedron: Asymmetry 16 2005 1829 1833
19. D. Steiner, L. Ivision, C.T. Goralski, R.B. Apell, J.R. Gojkovic, and B. Singaram Tetrahedron: Asymmetry 13 2002 2359 2363
20. L. Pu, and Y. Hong-Bin Chem. Rev. 101 2001 757 824
21. P.C. Andrews, M. Blair, B.H. Fraser, P.C. Junk, M. Massi, and L. Truck Tetrahedron: Asymmetry 17 2006 2833 2838
22. C. Cimarelli, D. Frationi, and G. Palmieri Tetrahedron: Asymmetry 20 2009 2234 2239
23. C.S. Graebin, V.L. Eifler-Lima, and R.G. da Rosa Catal. Commun. 9 2008 1066 1070
24. H. Mehrabi Can. J. Chem. 87 2009 1117 1121
25. M.V. Voronkov, A.V. Gontcharov, R.C. Kanamarlapudi, P.F. Richardson, and Z.-M. Wang OPRD 9 2005 221 224
26. M.V. Voronkov, R.C. Kanamarlapudi, and P. Richardson Tetrahedron Lett. 46 2005 6907 6910
27. Y.-Q. Yang, and G. Zhao Chem. Eur. J. 14 2008 10888 10891
28. R. Rasappan, and O. Reiser Eur. J. Org. Chem. 2009 1305 1308
29. S. Gladiali, and E. Alberico Chem. Soc. Rev. 35 2006 226 236
30. P. Roszkowski, and Z. Czarnocki Mini-Rev. Org. Chem. 4 2007 190 200
31. J.E.D. Martins, D.J. Morris, B. Tripathi, and M. Wills J. Organmet. Chem. 693 2008 3527 3532
32. E. Fuglseth, E. Sundby, and B.H. Hoff J. Fluorine Chem. 130 2009 600 603
33. Z. Zhou, Q. Ma, Y. Sun, A. Zhang, and L. Li Heteroatom Chem. 21 2010 505 514
34. S.V. Slungård, T.-A. Krakeli, T.H.K. Thvedt, E. Fuglseth, E. Sundby, and B.H. Hoff Tetrahedron 67 2011 5642 5650
35. V. Parekh, J.A. Ramsden, and M. Wills Catal. Sci. Technol. 2 2012 406 414
36. P. Roszkowski, J.K. Maurin, and Z. Czarnocki Tetrahedron: Asymmetry 23 2012 1106 1110
37. D. Sureshkumar, T. Gunasundari, V. Ganesh, and S. Chandrasekaran J. Org. Chem. 72 2007 2106 2117
38. J.U. Jeong, B. Tao, I. Sagasser, H. Henniges, and K.B. Sharpless J. Am. Chem. Soc. 120 1998 6844 6845
39. Y.G. Golobov, I.N. Zhmurova, and L.F. Kasukhin Tetrahedron 37 1981 437 472
40. W. Lin, X. Zhang, Z. He, Y. Jin, L. Gong, and A. Mi Synth. Commun. 32 2002 3279 3284
41. P. Roszkowski, J.K. Maurin, and Z. Czarnocki Synthesis 2012 241 246
42. G.M. Sheldrick Acta Cryst. A64 2008 112 122
43. H.D. Flack Acta Cryst. A39 1983 876 881