Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines

Tetrahedron

Volumn 60, Issue 41, 2004, Pages 9085-9091

  Chakraborti, Asit K ^a   Kondaskar, Atul ^a   Rudrawar, Santosh ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

2 Amino alcohol; Amines; Catalyst; Epoxide opening; Montmorillonite K 10; Selectivity

Indexed keywords

3 PHENOXYPROPYLENE OXIDE; ALKYL GROUP; AMINE; ANILINE; CYCLOALKENE; MONTMORILLONITE; PROPYLENE OXIDE; SOLVENT; STYRENE OXIDE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHELATION; DIASTEREOISOMER; ELECTRONICS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 4444252713     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.077     Document Type: Article

References (74)

1. J. Lieoscher, S. Jin, A. Otto, and K. Woydowski J. Heterocycl. Chem. 37 2000 509 518
2. D.R. Gehlert, D.J. Goldstein, and P.A. Hipskind Ann. Rep. Med. Chem. 1999 201 210
3. E.J. Corey, and F. Zhang Angew. Chem. Int. Ed. Engl. 38 1999 1931 1934
4. C.W. Johannes, M.S. Visser, G.S. Weatherhead, and A.H. Hoveyda J. Am. Chem. Soc. 120 1998 8340 8347
5. B.L. Chng, and A. Ganesan Bioorg. Med. Chem. Lett. 7 1997 1511 1514
6. J.D. Bloom, M.D. Dutia, B.D. Johnson, A. Wissner, M.G. Burns, E.E. Largis, J.A. Dolan, and T.H. Claus J. Med. Chem. 35 1992 3081 3084
7. L. Radesca, W.D. Bowen, L.D. Paolo, and B.R. de Costa J. Med. Chem. 34 1991 3058 3065
8. G.A. Rogers, S.M. Parsons, D.C. Anderson, L.M. Nilsson, B.A. Bahr, W.D. Kornreich, R. Kaufman, R.S. Jacobs, and B. Kirtman J. Med. Chem. 32 1989 1217 1230
9. J. De Cree, H. Geukens, J. Leempoels, and H. Verhaegen Drug Dev. Res. 8 1986 109 117
10. P. O'Brien Angew Chem. Int. Ed. Engl. 38 1999 326 329
11. G. Li, H.-T. Chang, and K.B. Sharpless Angew Chem. Int. Ed. Engl. 35 1996 451 454
12. D.J. Ager, I. Prakash, and D.R. Schaad Chem. Rev. 96 1996 835 876
13. S.C. Bergmeier Tetrahedron 56 2000 2561 2576
14. D.M. Hodgson, A.R. Gibbs, and G.P. Lee Tetrahedron 52 1996 14361 14384
15. R.M. Hanson Chem. Rev. 91 1991 437 475
16. (d) Comprehensive Organic Synthesis; Mitsunobu, O., Winterfeldt, E., Ed.; Pergamon: New York, 1996; Vol. 6, Pt 1.3.4.1.
17. A.S. Rao, S.K. Paknikar, and J.G. Kirtane Tetrahedron 39 1983 2323 2367
18. P.A. Crooks, and R. Szyudler Chem. Ind. (London) 1973 1111 1112
19. J.A. Deyrup, and C.L. Moyer J. Org. Chem. 34 1969 175 179
20. M. Freifelder, and G.R. Stone J. Org. Chem. 26 1961 1477 1480
21. M. Mousseron, J. Jullien, and Y. Jolchine Bull. Soc. Chim. Fr. 1952 757 766
22. R.E. Lutz, J.A. Freekand, and R.S. Murphy J. Am. Chem. Soc. 70 1948 2015 2023
23. G.H. Posner, and D.Z. Rogers J. Am. Chem. Soc. 99 1977 8208 8214
24. 2AlNHR: L.E. Overman, and L.A. Flippin Tetrahedron Lett. 22 1981 195 198
25. 2: M. Fiorenzo, A. Ricco, M. Tadder, and D. Tassi Synthesis 1983 640 641
26. (c) Silicon amides: A. Papini, I. Ricci, M. Taddei, G. Seconi, and P. Dembach J. Chem. Soc., Perkin Trans. 1 1984 2261 2265
27. 2NMgBr: M.C. Carre, J.P. Houmounou, and P. Caubere Tetrahedron Lett. 26 1985 3107 3110
28. 2: J.-I. Yamada, M. Yumoto, and Y. Yamamoto Tetrahedron Lett. 30 1989 4255 4258
29. (f) Cu amide: 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 1203
30. 2: J. Cossy, V. Bellosta, C. Hamoir, and J.-R. Desmurs Tetrahedron Lett. 43 2002 7083 7086
31. M. Chini, P. Crotti, and F. Macchia Tetrahedron Lett. 31 1990 4661 4664
32. 4SbOTf: M. Fujiwara, M. Imada, A. Baba, and H. Matsuda Tetrahedron Lett. 30 1989 739 742
33. 3: M. Chini, P. Crotti, L. Favero, F. Machhia, and M. Pineschi Tetrahedron Lett. 35 1994 433 436
34. 3: M. Meguro, N. Asao, and Y. Yamamoto J. Chem. Soc., Perkin Trans. 1 1994 2597 2601
35. (d) LiOTf J. Auge, and F. Leroy Tetrahedron Lett. 37 1996 7715 7716
36. 2: G. Sekar, and V.K. Singh J. Org. Chem. 64 1999 287 289
37. 3 T. Ollevier, and G. Lavie-Compin Tetrahedron Lett. 45 2004 49 52
38. 3: A. Sekine, T. Ohshima, and M. Shibasaki Tetrahedron 58 2002 75 82
39. 4: S. Sagava, H. Abe, Y. Hase, and T. Inaba J. Org. Chem. 64 1999 4962 4965
40. (c) DIPAT (diisopropoxyaluminium trifluoroacetate): S. Rampalli, S.S. Chaudhari, and K.G. Akamanchi Synthesis 2000 78 80
41. M. Curini, F. Epifano, M.C. Marcotullio, and O. Rosati Eur. J. Org. Chem. 2001 4149 4152
42. 2: J. Iqbal, and A. Pandey Tetrahedron Lett. 31 1990 575 576
43. 5: S. Chandrasekhar, T. Ramchander, and S.J. Prakash Synthesis 2000 1817 1818
44. 2 V. Weghe, and J. Collin Tetrahedron Lett. 36 1995 1649 1652
45. 3: X.-L. Fu, and S.-H. Wu Synth. Commun. 27 1997 1677 1684
46. 2: K. Fagnou, and M. Lautens Org. Lett. 2 2000 2319 2321
47. 3-NaI: L.R. Reddy, M.A. Reddy, N. Bhanumathi, and K.R. Rao Synthesis 2001 831 832
48. 3 T. Ollevier, and G. Lavie-Compin Tetrahedron Lett. 43 2002 7891 7893
49. 2: L.D. Pachón, P. Gamez, J.J.M. van Bassel, and J. Reedijk Tetrahedron Lett. 44 2003 6025 6027
50. 3: G. Sabitha, G.S.K.K. Reddy, K.B. Reddy, and J.S. Yadav Synthesis 2003 2298 2300
51. 4 A.K. Chakraborti, and A. Kondaskar Tetrahedron Lett. 44 2003 8315 8319
52. 4: P.-Q. Zhao, L.-W. Xu, and C.-G. Xia Synlett 2004 846 850
53. H. Kotsuki, T. Shimanouchi, M. Teraguchi, M. Kataoka, A. Tatsukawa, and H. Nishizawa Chem. Lett. 1994 2159 2162
54. R. Gupta, S. Paul, A.K. Gupta, P.L. Kachroo, and A. Dandia Ind. J. Chem. 36B 1997 281 283
55. U. Das, B. Crousse, V. Kesavan, D. Bonnet-Delpon, and J.-P. Bégué J. Org. Chem. 65 2000 6749 6751
56. J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah Tetrahedron Lett. 44 2003 1047 1050
57. R.-H. Fan, and X.-L. Hou J. Org. Chem. 68 2003 726 730
58. M. Shi, and Y. Chen J. Fluo. Chem. 122 2003 219 227
59. A.K. Chakraborti, S. Rudrawar, and A. Kondaskar Org. Biomol. Chem. 2 2004 1277 1280
60. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols. (a) C.E. Harris, G.B. Fisher, D. Beardsley, L. Lee, C.T. Goralsky, L.W. Nicholson, and B. Singaram J. Org. Chem. 59 1994 7746 7751
61. J. Yamada, Y. Yomoto, and Y. Yamamoto Tetrahedron Lett. 30 1989 4255 4258
62. J.K. Crandall, and M. Apparu Org. React. 29 1983 345 443
63. C.L. Kissel, and B. Rickborn J. Org. Chem. 37 1972 2060 2063
64. R.S. Varma Tetrahedron 58 2002 1235 1255
65. M.G. Clerici Topics Catal. 13 2000 373 386
66. K. Wilson, and J.H. Clark Pure Appl. Chem. 72 2000 1313 1319
67. M.M. Mojtahedi, M.R. Saidi, and M. Bolourtchian J. Chem. Res. (S) 1999 128 129
68. U.M. Lindstrom, B. Olofsson, and P. Somfai Tetrahedron Lett. 40 1999 9273 9276
69. C. Jaime, R.M. Ortuno, and J.J. Font J. Org. Chem. 53 1988 139 141
70. D.E. McLure, B.H. Arison, and J.J. Baldwin J. Am. Chem. Soc. 101 1979 3666 3668
71. R.G. Shanks, T.M. Wood, A.C. Dornshost, and M.L. Clark Nature 212 1966 88
72. A. Solladié-Cavello, and M. Bencheqroun J. Org. Chem. 57 1992 5831 5834
73. J.M. Klunder, S.Y. Ko, and K.B. Sharpless J. Org. Chem. 51 1986 3710 3712
74. P.W. Jeffs, J.F. Hansen, and G.A. Brine J. Org. Chem. 40 1975 2883 2890