An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines

Organic and Biomolecular Chemistry

Volumn 2, Issue 9, 2004, Pages 1277-1280

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

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

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CATALYSIS; MIXTURES; ORGANIC SOLVENTS; SILICA GEL; SYNTHESIS (CHEMICAL);

2-AMINO ALCOHOLS; EPOXIDE RINGS; UNNATURAL AMINO ACIDS;

ALCOHOLS;

AMINE; AMINOALCOHOL; EPOXIDE; SILICA GEL; SILICON DIOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; AMINO ALCOHOLS; CATALYSIS; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; SILICON DIOXIDE; STEREOISOMERISM;

EID: 2542462020     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b400588k     Document Type: Article

References (62)

1. (a) D. R. Gehlert, D. J. Goldstern and P. A. Hipskind, Annu. Rep. Med. Chem., 1999, 201;
2. (b) E. J. Corey and F. Zhang, Angew. Chem., Int. Ed. Engl., 1999, 38, 1931;
3. (c) C. W. Johannes, M. S. Visser, G. S. Weatherhead and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 8340;
4. (d) B. L. Chng and A. Ganesan, Bioorg. Med. Chem. Lett., 1997, 7, 1511;
5. (e) 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., 1989, 32, 1217;
6. (f) J, De Cree, H. Geukens, J. Leempoels and H. Verhaegen, Drug Dev. Res., 1986, 8, 109.
7. (a) P. O'Brien, Angew Chem., Int. Ed. Engl., 1999, 38, 326;
8. (b) G. Li, H.-T. Chang and K. B. Sharpless, Angew Chem., Int Ed. Engl., 1996, 35, 451.
9. D. J. Ager, I. Prakash and D. R. Schaad, Chem. Rev., 1996, 96, 835.
10. (a) S. C. Bergmeier, Tetrahedron, 2000, 56, 2561;
11. (b) D. M. Hodgson, A. R. Gibbs and G. P. Lee, Tetrahedron, 1996, 52, 14361;
12. (c) R. M. Hanson, Chem, Rev., 1991, 91, 437;
13. (d) O. Mitsunobu, in Comprehensive Organic Synthesis, ed. E. Winterfeldt, Pergamon Press, New York, 1996, Vol 6, Pt 1.3.4.1;
14. (e) A. S. Rao, S. K. Paknikar and J. G. Kirtane, Tetrahedron, 1983, 39, 2323.
15. (a) P. A. Crooks and R. Szyudler, Chem. Ind. (London), 1973, 1111;
16. (b) J. A. Deyrup and C. L. Moyer, J. Org. Chem., 1969, 34, 175;
17. (c) M. Freifelder and G. R. Stone, J. Org. Chem., 1961, 26, 1477;
18. (d) M. Mousseron, J. Jullien and Y. Jolchine, Bull. Soc. Chim. Fr., 1952, 757;
19. (e) R. E. Lutz, J. A. Freekand and R. S. Murphy, J. Am. Chem. Soc., 1948, 70, 2015.
20. G. H. Posner and D. Z. Rogers, J. Am. Chem. Soc., 1977, 99, 8208.
21. 2AlNHR: L. E. Overman and L. A. Flippin, Tetrahedron Lett., 1981, 22, 196;
22. (b) silicon amides: A. Papini, I. Ricci, M. Taddei, G. Seconi and P. Dembach, J. Chem. Soc., Perkin Trans., 1, 1984, 2261;
23. 2NMgBr: M. C. Carre, J. P. Houmounou and P. Caubere, Tetrahedron Lett., 1985, 26, 3107;
24. 2: J.-I. Yamada, M. Yumoto and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 4255;
25. (e) 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;
26. 2: J. Cossy, V. Bellosta, C. Hamoir and J.-R. Desmurs, Tetrahedron Lett., 2002, 43, 7083.
27. M. Chini, P. Crotti and F. Macchia, Tetrahedron Lett., 1990, 31, 4661.
28. 4SbOTf: M. Fujiwara, M. Imada, A. Baba and H. Matsuda, Tetrahedron Lett., 1989, 30, 739;
29. 3: M. Chini, P. Crotti, L. Favero, F. Machhia and M. Pineschi, Tetrahedron Lett., 1994, 35, 433;
30. 3: M. Meguro, N. Asao and Y. Yamamoto, J. Chem. Soc., Perkin Trans., 1, 1994, 2597;
31. (d) LiOTf: J. Auge and F. Leroy, Tetrahedron Lett., 1996, 37, 7715;
32. 2: G. Sekar and V. K. Singh, J. Org. Chem., 1999, 64, 287.
33. 4: S. Sagava, H. Abe, Y. Hase and T. Inaba, J. Org. Chem., 1999, 64, 4962;
34. (b) DIPAT (diisopropoxyaluminium trifluoroacetate): S. Rampalli, S. S. Chaudhari and K. G. Akamanchi, Synthesis, 2000, 78.
35. M. Curini, F. Epifano, M. C. Marcotullio and O. Rosati, Eur. J. Org. Chem., 2001, 4149.
36. 2: J. Iqbal and A. Pandey, Tetrahedron Lett., 1990, 31, 575;
37. 5: S. Chandrasekhar, T. Ramchander and S. J. Prakash, Synthesis, 2000, 1817;
38. 3: X.-L. Fu and S.-H. Wu, Synth. Commun., 1997, 27, 1677;
39. 3: L. R. Reddy, M. A. Reddy, N. Bhanumathi and K. R. Rao, Synthesis, 2001, 831;
40. 3: T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 2002, 43, 7891;
41. 2: L. D. Pachón, P. Gamez, J. J. M. van Bassel and J. Reedijk, Tetrahedron Lett., 2003, 44, 6025;
42. 3: G. Sabitha, G. S. K. K. Reddy, K. B. Reddy and J. S. Yadav, Synthesis, 2003, 2298;
43. 4: A. K. Chakraborti and A. Kondaskar, Tetrahedron Lett., 2003, 44, 8315.
44. (a) R. Gupta, S. Paul, A. K. Gupta, P. L. Kachroo and A. Dandia, Ind. J. Chem., 1997, 36B, 281;
45. (b) M. M. Mojtahedi, M. R. Saidi and M. Bolourtchian, J. Chem. Res. (S), 1999, 128.
46. U. Das, B. Crousse, V. Kesavan, D. Bonnet-Delpon and J.-P. Bégué, J. Org. Chem., 2000, 65, 6749.
47. J. S. Yadav, B. V. S. Reddy, A. K. Basak and A. V. Narsaiah, Tetrahedron Lett., 2003, 44, 1047.
48. R.-H. Fan and X.-L. Hou, J. Org. Chem., 2003, 68, 726.
49. M. Shi and Y. Chen, J. Fluorine Chem., 2003, 122, 219.
50. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols, (a) J. Yamada, Y. Yomoto and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 4255; (b) J. K. Crandall and M. Apparu, Org. React., 1983, 29, 345; (c) J. K. Whitesel and S. W. Felman, J. Org. Chem., 1980, 45, 755; (d) C. L. Kissel and B. Rickborn, J. Org. Chem., 1972, 37, 2060.
51. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols, (a) J. Yamada, Y. Yomoto and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 4255; (b) J. K. Crandall and M. Apparu, Org. React., 1983, 29, 345; (c) J. K. Whitesel and S. W. Felman, J. Org. Chem., 1980, 45, 755; (d) C. L. Kissel and B. Rickborn, J. Org. Chem., 1972, 37, 2060.
52. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols, (a) J. Yamada, Y. Yomoto and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 4255; (b) J. K. Crandall and M. Apparu, Org. React., 1983, 29, 345; (c) J. K. Whitesel and S. W. Felman, J. Org. Chem., 1980, 45, 755; (d) C. L. Kissel and B. Rickborn, J. Org. Chem., 1972, 37, 2060.
53. Metal alkylamides induce the rearrangement of epoxides to allylic alcohols, (a) J. Yamada, Y. Yomoto and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 4255; (b) J. K. Crandall and M. Apparu, Org. React., 1983, 29, 345; (c) J. K. Whitesel and S. W. Felman, J. Org. Chem., 1980, 45, 755; (d) C. L. Kissel and B. Rickborn, J. Org. Chem., 1972, 37, 2060.
54. J. Elkington, http://www.sustainability.co.uk/sustainability.httm.
55. G. W. Kabalka and R. M. Pagni, Tetrahedron, 1997, 53, 7999.
56. (a) A. McKillop and D. W. Young, Synthesis, 1979, 401;
57. (b) A. McKillop and D. W. Young, Synthesis, 1979, 481.
58. 3 are not effective for reactions with aliphatic amines.
59. S. A. Anderson, J. T. Ayers, K. M. DeVries, F. Ito, D. Mendenhall and B. C. Vanderplas, Tetrahedron: Asymmetry, 1999, 10, 2655.
60. D. E. McClure, B. H. Arison and J. J. Baldwin, J. Am. Chem. Soc., 1979, 101, 3666.
61. R. L. Garrett, in Designing Safer Chemicals, R. L. Garrett and S. C. De Vilto, eds., American Chemical Society Symposium Series 640, Washington DC, 1996, Chapter 1.
62. X.-L. Hou, J. Wu, L.-X. Dai, L.-J. Xia and M.-H. Tang, Tetrahedron: Asymmetry, 1998, 9, 1747.