Synthesis of nitrile coordinated Lewis acids Al(OC(CF3) 2R)3 and their application in catalytic epoxide ring-opening reactions

Applied Catalysis A: General

Volumn 384, Issue 1-2, 2010, Pages 171-176

  Li, Yang ^a   Tan, Yi ^a   Herdtweck, Eberhardt ^a   Cokoja, Mirza ^a   Kühn, Fritz E ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Aluminum; Epoxides; Homogeneous catalysis; Lewis acid; Ring opening reaction

Indexed keywords

AMINO ALCOHOLS; EPOXIDE RING-OPENING REACTION; EPOXIDES; HIGH YIELD; HOMOGENEOUS CATALYSIS; LEWIS ACID; RING OPENING REACTION; ROOM TEMPERATURE; SOLVENT FREE CONDITIONS;

ACIDS; ALCOHOLS; ALUMINUM; AMINATION; AMINES; CATALYSIS; CATALYSTS; CYANIDES; INFRARED SPECTROSCOPY; MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

COORDINATION REACTIONS;

EID: 77955661648     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2010.06.029     Document Type: Article

References (52)

1. K.B. Lindsay, and S.G. Pyne Tetrahedron 60 2004 4173
2. E. Ruediger, A. Martel, N. Meanwell, C. Solomon, and B. Turmel Tetrahedron Lett. 45 2004 739
3. P. O'Brien Angew. Chem. Int. Ed. 38 1999 326
4. G.G. Li, H.T. Chang, and K.B. Sharpless Angew. Chem. Int. Ed. 35 1996 451
5. D.J. Ager, I. Prakash, and D.R. Schaad Chem. Rev. 96 1996 835
6. L.E. Overman, and L.A. Flippin Tetrahedron Lett. 22 1981 196
7. M.C. Carre, J.P. Houmounou, and P. Caubere Tetrahedron Lett. 26 1985 3107
8. Y. Yamamoto, N. Asao, M. Meguro, N. Tsukade, H. Nemoto, N. Adayari, J.G. Wilson, and H. Nakamura J. Chem. Soc., Chem. Commun. 1993 1201
9. J. Cossy, V. Bellosta, C. Hamoir, and J.-R. Desmurs Tetrahedron Lett. 43 2002 7083
10. S. Sagava, H. Abe, Y. Hase, and T. Inaba J. Org. Chem. 64 1999 4962
11. S. Rampalli, S.S. Chaudhari, and K.G. Akamanchi Synthesis 2000 78
12. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Eur. J. Org. Chem. 2001 4149
13. M. Chini, P. Crotti, and F. Macchia Tetrahedron Lett. 31 1990 4661
14. J. Iqbal, and A. Pandey Tetrahedron Lett. 31 1990 575
15. C. Bonini, and G. Righi Synthesis 1994 225
16. B.L. Chng, and A. Ganesan Bioorg. Med. Chem. Lett. 7 1997 1511
17. X.L. Fu, and S.H. Wu Synth. Commun. 27 1997 1677
18. S. Chandrasekhar, T. Ramachandar, and S.J. Prakash Synthesis 2000 1817
19. L.R. Reddy, M.A. Reddy, N. Bhanumathi, and K.R. Rao Synthesis 2001 831
20. J. Auge, and F. Leroy Tetrahedron Lett. 37 1996 7715
21. D. Brandley, G. Williams, and M. Lawton Org. Biomol. Chem. 3 2005 3269
22. B. Shivani, A.K. Pujala, and Chakraborti J. Org. Chem. 72 2007 3713
23. M. Fujiwara, M. Imada, A. Baba, and H. Matsuda Tetrahedron Lett. 30 1989 739
24. G. Sekar, and V.K. Singh J. Org. Chem. 64 1999 287
25. G.H. Posner, and D.Z. Rogers J. Am. Chem. Soc. 99 1977 8208
26. M. Onaka, M. Kawai, and Y. Izumi Chem. Lett. 1985 779
27. J. Yamada, M. Yumoto, and Y. Yamamoto Tetrahedron Lett. 30 1989 4255
28. G. Erker Dalton Trans. 2005 1883
29. M. Bochmann J. Chem. Soc., Dalton Trans. 1996 255
30. E.Y.-X. Chen, and T.J. Marks Chem. Rev. 100 2000 1391
31. M.C. Baird Chem. Rev. 100 2000 1471
32. S. Chandrasekhar, C.R. Reddy, B.N. Babu, and G. Chandrashekar Tetrahedron Lett. 43 2002 3801
33. I.D.G. Watson, and A.K. Yudin J. Org. Chem. 68 2003 5160
34. G.C. Welch, R.R.S. Juan, J.D. Masuda, and D.W. Stephan Science 314 2006 1124
35. P.A. Chase, and D.W. Stephan Angew. Chem. Int. Ed. 47 2008 7433
36. D. Holschumacher, T. Bannenberg, C.G. Hrib, P.G. Jones, and M. Tamm Angew. Chem. Int. Ed. 47 2008 7428
37. T.A. Rokob, A. Hamza, A. Stirling, T. Soos, and I. Papai Angew. Chem. Int. Ed. 47 2008 2435
38. V. Sumerin, F. Schulz, M. Nieger, M. Leskela, T. Repo, and B. Rieger Angew. Chem. Int. Ed. 47 2008 6001
39. M.J. Collins, and G.J. Schrobilgen Inorg. Chem. 24 1985 2608
40. F. Sladky, H. Kropshof, and O. Leitzke J. Chem. Soc., Chem. Commun. 1973 134
41. V.C. Williams, W.E. Piers, W. Clegg, M.R.J. Elsegood, S. Collins, and T.B. Marder J. Am. Chem. Soc. 121 1999 3244
42. L.O. Müller, D. Himmel, J. Stauffer, G. Steinfeld, J. Slattery, G. Santiso-Quinones, V. Brecht, and I. Krossing Angew. Chem. Int. Ed. 47 2008 7659
43. A.K. Chakraborti, S. Rudrawar, and A. Kondaskar Eur. J. Inorg. Chem. 2004 3597
44. A.K. Chakraborti, and A. Kondaskar Tetrahedron Lett. 44 2003 8315
45. A.K. Chakraborti, S. Rudrawar, and A. Kondaskar Org. Biomol. Chem. 2 2004 1277
46. A.K. Chakraborti, A. Kondaskar, and S. Rudrawar Tetrahedron 60 2004 9085
47. K. Starowieyski, S. Pasynkiewicz, and M. Boleslawski J. Organomet. Chem. 10 1967 393
48. C.H. Lee, S.J. Lee, J.W. Park, K.H. Kim, B.Y. Lee, and J.S. Oh J. Mol. Catal. A: Chem. 132 1998 231
49. H. Jacobsen, H. Berke, S. Doring, G. Kehr, G. Erker, R. Frohlich, and O. Meyer Organometallics 18 1999 1724
50. R.T. Henriques, E. Herdtweck, F.E. Kühn, A.D. Lopes, J. Mink, and C.C. Romão J. Chem. Soc., Dalton Trans. 1998 1293
51. M. Berthelot, M. Helbert, C. Laurence, and J.-Y.L. Questel J. Phys. Org. Chem. 6 1993 302
52. J.-Y.L. Questel, M. Berthelot, and C. Laurence J. Phys. Org. Chem. 13 2000 347