A facile and efficient synthesis of β-amino alcohols using 2,2,2-trifluoroethanol as a metal-free and reusable medium

Journal of Fluorine Chemistry

Volumn 131, Issue 1, 2010, Pages 106-110

  Khaksar, Samad ^a   Heydari, Akbar ^a   Tajbakhsh, Mahmood ^b   Bijanzadeh, Hamid Reza ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Amino alcohols; Hydrogen bonding; Regioselectivity; TFE

Indexed keywords

EID: 71249100190     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.10.003     Document Type: Article

References (61)

1. Nielsen L.P.C., and Jacobsen E.N. In: Yudin A.K. (Ed). Aziridine and Epoxides in Organic Synthesis (2006), Wiely-VCH, Weinheim
2. Pastor I.M., and Yus M. Curr. Org. Chem. 9 (2005) 1-29
3. Bandini M., Melloni A., Tommasi S., and Umani-Ronchi A. Synlett (2005) 1199-1222
4. Corey E.J., and Zhang F. Angew. Chem. Int. Ed. Engl. 348 (1999) 1931-1934
5. O'Brien P. Angew. Chem. Int. Ed. Engl. 38 (1999) 326-329
6. Bose D.S., and Narsaiah A.V. Bioorg. Med. Chem. 3 (2005) 627-630
7. Erhardt P.W., Woo C.W., and Anderson W.G. J. Med. Chem. 25 (1982) 1408-1412
8. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-875
9. Lindasy K.B., and Pyne S.G. Tetrahedron 60 (2004) 4173-4176
10. Zhu S., Meng L., Zhang Q., and Wei L. Bioorg. Med. Chem. Lett. 16 (2006) 1854-1858
11. Moore W.J., and Luzzzio F.A. Tetrahedron Lett. 36 (1995) 6599-6602
12. Wu M.H., and Jacobsen E.N. Tetrahedron Lett. 38 (1997) 1693-1696
13. Bergmeier S.C. Tetrahedron 56 (2000) 2561-2576
14. Deyrup J.A., and Moyer C.L. J. Org. Chem. 34 (1969) 175-179
15. Crooks P.A., and Szyudler R. Chem. Ind. (London) (1973) 1111-1112
16. Sekar G., and Singh V.K.J. Org. Chem. 64 (1999) 287-289
17. Yadav J.S., Reddy A.R., Narsaiah A.V., and Reddy B.V.S. J. Mol. Cat. A: Chem. 261 (2007) 207-212
18. Williams D.B.G., and Lawton M. Tetrahedron Lett. 47 (2006) 6557-6560
19. Procopio A., Gaspari M., Nardi M., Oliverio M., and Rosati O. Tetrahedron Lett. 49 (2008) 2289-2293
20. Reddy L.R., Reddy M.A., Bhanumathi N., and Rao K.R. New J. Chem. 25 (2001) 221-222
21. Ollevier T., and Lavie-Compin G. Tetrahedron Lett. 43 (2002) 7891-7893
22. Singh M.C., and Peddinti R.K. Tetrahedron Lett. 48 (2007) 7354-7357
23. Chakraborti A.K., and Kondaskar A. Tetrahedron Lett. 44 (2003) 8315-8319
24. Rodri{dotless}́guez J.R., and Navarro A. Tetrahedron Lett. 45 (2004) 7495-7498
25. Sundararajan G., Vijayakrishna K., and Varghese B. Tetrahedron Lett. 45 (2004) 8253-8256
26. Kamal A., Ramu R.R., Azhar M.A., and Khanna G.B.R. Tetrahedron Lett. 46 (2005) 2675-2677
27. Maheswara M., Rao K.S.V.K., and Do J.Y. Tetrahedron Lett. 49 (2008) 1795-1800
28. Yadav J.S., Reddy B.V.S., Basak A.K., and Narasaiah A.V. Tetrahedron Lett. 44 (2003) 1047-1050
29. Kotsuki H., Shimanouchi T., Teraguchi M., Kataoka M., Tatsukawa A., and Nishizawa H. Chem. Lett. (1994) 2159-2162
30. Chakraborti A.K., Rudrawar S., and Kondaskar A. Org. Biomol. Chem. 2 (2004) 1277-1280
31. Reddy B.M., Patil K.M., Reddy B.T., and Park S.E. Catal. Commun. 9 (2008) 950-954
32. Bhanushali M.J., Nandurkar N.S., Bhor M.D., and Bhanage B.M. Tetrahedron Lett. 49 (2008) 3672-3676
33. Cossy J., Bellosta V., Hamoir C., and Desmurs J.R. Tetrahedron Lett. 43 (2002) 7083-7086
34. Reichardt C. Chem. Rev. 94 (1994) 2319-2358
35. Klement I., Luetjens H., and Knochel P. Angew. Chem., Int. Ed. Engl. 36 (1997) 1454-1456
36. From the data of solvolytic studies, the ionizing power Y for HFIP is 3.61 (cf. Y = 3.04 for HCOOH), see: F.L. Schadt, T.W. Bentley, P. von R. Schleyer, J. Am. Chem. Soc. 98 (1976) 7667-7674.
37. Minegishi S.S., Kobayashi S., and Mayr H. J. Am. Chem. Soc. 126 (2004) 5174-5181
38. Denegri B., Minegishi S., Kronja O., and Mayr H. Angew. Chem. Int. Ed. 43 (2004) 2302-2305
39. Mayr H., Kempf B., and Ofial A.F. Acc. Chem. Res. 36 (2003) 66-77
40. Hofmann M., Hampel N., Kanzian T., and Mayr H. Angew. Chem. Int. Ed. 43 (2004) 5402-5405
41. Westermaier M., and Mayr H. Org. Lett. 8 (2006) 4791-4794
42. Kevill D.N., and D'Souza M.J. J. Phys. Org. Chem. 15 (2002) 881-888
43. Richard J.P., Toteva M.M., and Amyes T.L. Org. Lett. 3 (2001) 2225-2228
44. Liu K.T., and Chen H.I. J. Chem. Soc., Perkin Trans. 2 (2000) 893-898
45. Schadt F.L., Bentley T.V., and Schleyer P.V.R. J. Am. Chem. Soc. 98 (1976) 7667-7674
46. Heydari A., Khaksar S., and Tajbakhsh M. Synthesis 19 (2008) 3126-3130
47. Heydari A., Khaksar S., and Tajbakhsh M. Tetrahedron Lett. 50 (2009) 77-80
48. Heydari A., Khaksar S., Tajbakhsh M., and Bijanzadeh H.R. J. Fluorine Chem. 130 (2009) 609-614
49. Ben-Daniel R., De Visser S.P., Shaik S., and Neumann R. J. Am. Chem. Soc. 125 (2003) 12116-12117
50. Habusha U., Rozental E., and Hoz S. J. Am. Chem. Soc. 124 (2002) 15006-15011
51. Abe H., Amii H., and Uneyama K. Org. Lett. 3 (2001) 313-315
52. Bégué J.P., Bonnet-Delpon D., and Crousse B. Synlett (2004) 18-29
53. Iskra J., Bonnet-Delpon D., and Bégué J.P. Tetrahedron Lett. 43 (2002) 1001-1003
54. Legros J., Crousse B., Bonnet-Delpon D., and Bégué J.-P. Eur. J. Org. Chem. (2002) 3290-3293
55. Ravikumar K.S., Zhang Y.M., Bégué J.P., and Bonnet-Delpon D. Eur. J. Org. Chem. (1998) 2937-2940
56. Kobayashi S., Tanaka H., Amii H., and Uneyama K. Tetrahedron 59 (2003) 1547-1552
57. Berkessel A., Andreae M.R.M., Schmickler H., and Lex J. Angew. Chem. Int. Ed. 4 (2002) 4481-4484
58. Das U., Crousse B., Kesavan V., Bonnet-Delpon D., and Begue J.P. J. Org. Chem. 65 (2000) 6749-6751
59. Uneyama K. Organofluorine Chemistry (2006), Blackwell Publishing, Oxford, UK
60. Philippe C., Milcent T., Crousse B., and Bonnet-Delpon D. Org. Biomol. Chem. 7 (2009) 2026-2028
61. Westermaier M., and Mayr H. Chem. Eur. J. 14 (2008) 1638-1647