Synthesis of proline derivatives of bile acids and their evaluation as organocatalysts in the asymmetric direct aldol reaction

Tetrahedron Asymmetry

Volumn 18, Issue 11, 2007, Pages 1364-1375

  Puleo, Gian Luigi ^a,b   Masi, Matteo ^b   Iuliano, Anna ^b  

^a SCUOLA NORMALE SUPERIORE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZALDEHYDE; ACETONE; AMINO ACID DERIVATIVE; BENZALDEHYDE DERIVATIVE; BILE ACID; CHOLIC ACID; DEOXYCHOLIC ACID; HYDROXYL GROUP; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 34447101015     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.05.023     Document Type: Article

References (57)

1. Berkessel A., and Gröger H. Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
2. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
3. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
4. Notz W., and List B. J. Am. Chem. Soc. 122 (2000) 7386-7387
5. Dalko P.I., and Moisan L. Angew. Chem. 113 (2001) 3840-3864
6. Benaglia M., Puglisi A., and Cozzi F. Chem. Rev. 103 (2003) 3401
7. In: Schmalz H.-G., and Wirth T. (Eds). Organic Synthesis Highlights V (2003), Wiley-VCH, Weinheim
8. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
9. Special issue: Asymmetric Organocatalysis:. Acc. Chem. Res. 37 (2004) 487-631
10. Seayade J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
11. List B. Chem. Commun. 8 (2006) 819-824
12. Brogan A.P., Dickerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 45 (2006) 8100-8102
13. List B. Asym. Synth. (2007) 161-165
14. Ley S.V. Asym. Synth. (2007) 201-206
15. Cobb A.J.A., Shaw D.M., Longbottom D.A., Gold J.B., and Ley S.V. Org. Biomol. Chem. 3 (2005) 84-96
16. Chen J.-R., Lu H.-H., Li X.-Y., Cheng L., Wan J., and Xiao W.-J. Org. Lett. 7 (2005) 4543-4545
17. Gryko D., and Lipinski R. Adv. Synth. Catal. 347 (2005) 1948-1952
18. Samanta S., Liu J., Dodda R., and Zhao C.-G. Org. Lett. 7 (2005) 5321
19. Tang Z., Cun L.-F., Cui X., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Org. Lett. 8 (2006) 1263-1266
20. Raj M., Vishnumaya M.R., Ginotra S.K., and Singh V.K. Org. Lett. 8 (2006) 4097-4099
21. Chimni S.S., and Mahajan D. Tetrahedron: Asymmetry 17 (2006) 2108-2119
22. Wang Y., Wei S., and Sun J. Synlett (2006) 3319-3323
23. Pandey J., Dwivedi N., Singh N., Srivastava A.K., Tamarkar A., and Tripathi R.P. Bioorg. Med. Chem. Lett. 17 (2007) 1321-1325
24. Guizzetti S., Benaglia M., Raimondi L., and Celentano G. Org. Lett. 9 (2007) 1247-1250
25. Hayashi Y., Tsuboi W., Ashimine I., Urushima T., Shoji M., and Sakai K. Angew. Chem., Int. Ed. 42 (2003) 3677-3680
26. Cobb A.J.A., Shaw D.M., and Ley S.V. Synlett (2004) 558-560
27. Ibrahem I., Zou W., Engqvist M., Xu Y., and Cordova A. Chem. Eur. J. 11 (2005) 7024-7029
28. Sasaoka A., Uddin Md.I., Shimomoto A., Ichikawa Y., Shiro M., and Kotsuki H. Tetrahedron: Asymmetry 17 (2006) 2963-2969
29. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559-2561
30. Cobb A.J.A., Longbottom D.A., Shaw D.M., and Ley S.V. Chem. Commun. 16 (2004) 1808-1809
31. Mitchell C.E.T., Cobb A.J.A., and Ley S.V. Synlett (2005) 611-614
32. Hayashi Y., Gotoh H., Hayashy T., and Shoji M. Angew. Chem., Int. Ed. 44 (2005) 4212-4215
33. Yan Z.-Y., Niu Y.-N., Wei H.-L., Wu L.-Y., Zhao Y.-B., and Liang Y.-M. Tetrahedron: Asymmetry 17 (2006) 3288-3293
34. Kirby A.J. Angew. Chem., Int. Ed. 35 (1996) 706-724
35. Heine A., De Santis G., Luz J.G., Mitchell M., Wong C.-H., and Wilson I.A. Science 294 (2001) 294-369
36. Iuliano A., Salvadori P., and Felix G. Tetrahedron: Asymmetry 10 (1999) 3353-3364
37. Iuliano A., Masini G., Salvadori P., and Félix G. Tetrahedron: Asymmetry 12 (2001) 2811-2825
38. Iuliano A., Pieraccini I., Félix G., and Salvadori P. Tetrahedron: Asymmetry 13 (2002) 1265-1275
39. Iuliano A., and Scafato P. Tetrahedron. Asymmetry 14 (2003) 611-618
40. Iuliano A., and Felix G. J. Chromatogr., A 1031 (2004) 187-195
41. Iuliano A., Scafato P., and Torchia R. Tetrahedron: Asymmetry 15 (2004) 2533-2538
42. Iuliano A., and Ruffini A. Tetrahedron: Asymmetry 16 (2005) 3820-3828
43. Iuliano A., Facchetti S., and Uccello Barretta G. J. Org. Chem. 71 (2006) 4943-4950
44. Allemann C., Gordillo R., Clemente F.R., Cheong P.H.-Y., and Houk K.N. Acc. Chem. Res. 37 (2004) 558-569
45. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580-591
46. Fieser L.F., and Rajagopalan S. J. Am. Chem. Soc. (1950) 5530-5536
47. Davis A.P., and Perez-Payan M.N. Synlett (1999) 991-993
48. Li C., Rehman A.-U., Dalley N.K., and Savage P.B. Tetrahedron Lett. 40 (1999) 1861-1864
49. Broderick S., Davis A.P., and Williams R.P. Tetrahedron Lett. (1998) 6083-6086
50. Davis A.P., and Lawless L.J. Chem. Commun. (1999) 9-10
51. Barry J.F., Davis A.P., and Perez-Payan M.N. Tetrahedron Lett. 40 (1999) 2849-2852
52. Baker J.F., and Blickenstaff R.T. J. Org. Chem. 40 (1975) 1579-1586
53. Kurtz K.C.M., Hsung R.P., and Zhang Y. Org. Lett. 8 (2006) 231-234
54. Ciajolo M.R., Tuzi A., Pratesi C.R., Fissi A., and Pieroni O. Biopolymers 10 (1990) 911-920
55. Chang F.C. J. Org. Chem. 44 (1979) 4567-4572
56. Alagona G., Ghio C., Iuliano A., Monti S., Pieraccini I., and Salvadori P. J. Org. Chem. 68 (2003) 3145-3157
57. It is difficult to currently explain these results. We can hypothesize that water accelerates the reaction because it takes place in a 'concentrated organic phase' constituted by the cleft of the organocatalyst:. Mase N., Nakai Y., Ohara N., Yoda H., Takabe K., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 734-735