Chiral amino alcohols derived from natural amino acids as chiral solvating agents for carboxylic acids

Tetrahedron Asymmetry

Volumn 19, Issue 10, 2008, Pages 1193-1199

  Wang, Wenge ^a   Shen, Xiumin ^a   Ma, Fengnian ^a   Li, Zijing ^a   Zhang, Cong ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMINO ALCOHOL DERIVATIVE; AMINOALCOHOL; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; STOICHIOMETRY;

EID: 44449157182     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.030     Document Type: Article

References (53)

1. Parker D. Chem. Rev. 91 (1991) 1441-1457
2. Wenzel T.J., and Wilcox J.D. Chirality 15 (2003) 256-270
3. Pirkle W.H., and Hoover D.J. Top. Stereochem. 13 (1982) 263-331
4. Uccello-Barretta G., Balzano F., Menicagli R., and Salvadori P. J. Org. Chem. 61 (1996) 363-365
5. Fulwood R., and Parker D. Tetrahedron: Asymmetry 3 (1992) 25-28
6. Kühn M., and Buddrus J. Tetrahedron: Asymmetry 4 (1993) 207-210
7. Fulwood R., and Parker D. J. Chem. Soc., Perkin Trans. 2 (1994) 57-64
8. Port A., Virgili A., and Jaime C. Tetrahedron: Asymmetry 7 (1996) 1295-1302
9. Baily D.J., O'Hagan D., and Tavasli M. Tetrahedron: Asymmetry 8 (1997) 149-153
10. Uccello-Barretta G., Iuliano A., Franchi E., Balzano F., and Salvadori P. J. Org. Chem. 63 (1998) 9197-9203
11. Enders D., Thomas C.R., and Runsink J. Tetrahedron: Asymmetry 10 (1999) 323-326
12. Uccello-Barretta G., Samaritani S., Menicagli R., and Salvadori P. Tetrahedron: Asymmetry 11 (2000) 3901-3912
13. Port A., Virgili A., Alvarez-Larena A., and Piniella J.F. Tetrahedron: Asymmetry 11 (2000) 3747-3757
14. Iuliano A., Uccello-Barretta G., and Salvadori P. Tetrahedron: Asymmetry 11 (2000) 1555-1563
15. Rajamoorthi K., and Stockton W. Spectrosc. Lett. 34 (2001) 255-266
16. Yang X., Wang G., Zhong C., Wu X., and Fu E. Tetrahedron: Asymmetry 17 (2006) 916-921
17. Wang W., Ma F., Shen X., and Zhang C. Tetrahedron: Asymmetry 18 (2007) 832-837
18. Pérez-Trujillo M., Maestre I., Jaime C., Alvarez-Larena A., Piniella J.F., and Virgili A. Tetrahedron: Asymmetry 16 (2005) 3084-3093
19. Pirkle W.H., Sikkenga D.L., and Pavlin M.S. J. Org. Chem. 42 (1977) 384-387
20. Pérez-Trujillo M., and Virgili A. Tetrahedron: Asymmetry 17 (2006) 2842-2846
21. Pérez-Trujillo M., Virgili A., and Molins E. Tetrahedron: Asymmetry 15 (2004) 1615-1621
22. Beaufour M., Merelli B., Menguy L., and Cherton J.-C. Chirality 15 (2003) 382-390
23. Pirkle W.H., Sikkenga D.L., and Pavlin M.S. J. Org. Chem. 42 (1977) 1370-1374
24. Villani F.J., Costanzo M.J., Inners R.R., Mutter M.S., and McClure D.E. J. Org. Chem. 51 (1986) 3715-3718
25. Muñoz A., and Virgili A. Tetrahedron: Asymmetry 17 (2002) 1529-1534
26. Ridder D., Wunderlich H., and Braun M. Eur. J. Org. Chem. (1998) 1071-1076
27. Jullian J.-C., Franc X., Latypov S., Hocquemiller R., and Figadère B. Tetrahedron: Asymmetry 14 (2003) 963-966
28. Pirkle W.H., Muntz R.L., and Paul I.C. J. Am. Chem. Soc. 93 (1971) 2817-2819
29. Bussche-Hünnefeld C., Beck A.K., Lengweiler U., and Seebach D. Helv. Chim. Acta 75 (1992) 438-441
30. Moragas M., Cervelló E., Port A., Jaime C., Virgili A., and Ancian B. J. Org. Chem. 63 (1998) 8689-8695
31. Fukui H., Fukushi Y., and Tahara S. Tetrahedron Lett. 44 (2003) 4063-4065
32. Comelles J., Estivill C., Moreno-Mañas M., Virgili A., and Vallribera A. Tetrahedron 60 (2004) 11541-11546
33. Almer S., Cervelló E., Jaime C., and Virgili A. Tetrahedron: Asymmetry 10 (1999) 3719-3725
34. Ferreiro M.J., Latypov S.K., Quiñoá E., and Riguera R. J. Org. Chem. 65 (2000) 2658-2666
35. Rosini C., Uccello-Barretta G., Pini D., Abete C., and Salvadori P. J. Org. Chem. 53 (1988) 4579-4581
36. Uccello-Barretta G., Bardoni S., Balzano F., and Salvadori P. Tetrahedron: Asymmetry 12 (2001) 2019-2023
37. Uccello-Barretta G., Mirabella F., Balzano F., and Salvadori P. Tetrahedron: Asymmetry 14 (2003) 1511-1516
38. Guevas F., Ballester P., and Pericàs M.A. Org. Lett. 7 (2005) 5485-5487
39. Shirakawa S., Moriyama A., and Shimizu S. Org. Lett. 9 (2007) 3117-3119
40. Zheng Y.-S., and Zhang C. Org. Lett. 6 (2004) 1189-1192
41. Itsuno S., and Ito K. J. Org. Chem. 49 (1984) 555-557
42. Wu Y.-J., Yun H.-Y., Wu Y.-S., Ding K.-L., and Zhou Y. Tetrahedron: Asymmetry 11 (2000) 3543-3552
43. Da C.S., Han Z.J., Ni M., Yang F., Liu D.X., Zhou Y.F., and Wang R. Tetrahedron: Asymmetry 14 (2003) 659-665
44. Kanth J.V.B., and Periasamy M. J. Org. Chem. 56 (1991) 5964-5965
45. McKennon M.J., Meyers A.I., Drauz K., and Schwarm M. J. Org. Chem. 58 (1993) 3568-3571
46. Itsuno S., Sakurai Y., Ito K., Hirao A., and Nakahama S. Bull. Chem. Soc. Jpn. 60 (1987) 395-398
47. Itsuno S., Sakurai Y., Ito K., Nakahama S., and Frechet J.M.J. J. Org. Chem. 55 (1990) 304-310
48. Kohra S., Hayashida H., Tominaga Y., and Hosomi A. Tetrahedron Lett. 29 (1988) 89-92
49. Anna I., Debora B., Gloria U.-B., Federica B., and Piero S. Eur. J. Org. Chem. (2001) 2177-2184
50. Crystallographic data for the structure of compound 5b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 663276. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
51. Wenzel T.J., and Thurston J.E. Tetrahedron Lett. 41 (2000) 3769-3772
52. Fielding L. Tetrahedron 56 (2000) 6151-6170
53. Macleod C., Mckiernan G.J., Guthrie E.J., Farrugia L.J., Hamprecht D.W., Macritchie J., and Hartley R.C. J. Org. Chem. 68 (2003) 387-401