Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols

Tetrahedron Asymmetry

Volumn 18, Issue 23, 2007, Pages 2758-2767

  Tiecco, Marcello ^a   Testaferri, Lorenzo ^a   Bagnoli, Luana ^a   Scarponi, Catalina ^a   Temperini, Andrea ^a   Marini, Francesca ^a   Santi, Claudio ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLGLYCINOL; 2,5 PYRROLIDINE; AMINOALCOHOL; BETA AMINO SELENIDE; PYRROLIDINE DERIVATIVE; SELENIDE; SELENIUM; TRIPHENYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 36649002679     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.11.003     Document Type: Article

References (57)

1. Lewis J.R. Nat. Prod. Rep. 18 (2001) 95
2. O'Hagan D. Nat. Prod. Rep. 17 (2000) 435
3. Watson P.S., Jiang B., and Scott B. Org. Lett. 2 (2000) 3679
4. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., and Nash R.J. Phytochemistry 56 (2001) 265
5. Goti A., Cicchi S., Mannucci V., Cardona F., Guarna F., Merino P., and Tejero T. Org. Lett. 5 (2003) 4235
6. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138
7. Shi Y. Acc. Chem. Res. 37 (2004) 488
8. Kim B.H., Lee H.B., Hwang J.K., and Kim Y.G. Tetrahedron: Asymmetry 16 (2005) 1215
9. Sweet J.A., Cavallari J.M., Price W.A., Ziller J.W., and McGrath D.V. Tetrahedron: Asymmetry 8 (1997) 207
10. Wang Q., Sasaki A.N., Riche C., and Potier P. J. Org. Chem. 64 (1999) 8602
11. Davis A.F., Song M., and Augustine A. J. Org. Chem. 71 (2006) 2779 and references cited therein
12. Shao Z.H., Peng F.Z., Zhu B.K., Tu Y.Q., and Zhang H.B. Chin. J. Chem. 22 (2004) 727 and references cited therein
13. Viso A., Lee N.E., and Buchwald S.L. J. Am. Chem. Soc. 116 (1994) 9373
14. Yun J., and Buchwald S.L. Chirality 12 (2000) 476
15. Wu S., Lee S., and Beak P. J. Am. Chem. Soc. 118 (1996) 715
16. Jones A.D., Redfern A.L., Knight D.W., Morgan I.R., and Williams A.C. Tetrahedron 62 (2006) 9247 and references cited therein
17. Clive D.L.J., Farina V., Singh A., Wong C.K., Kiel W.A., and Menchen S.M. J. Org. Chem. 45 (1980) 2120
18. Morella A.M., and Ward A.D. Aust. J. Chem. 48 (1995) 445
19. De Kimpe N., and Boelens M. J. Chem. Soc., Chem. Commun. (1993) 916
20. Tiecco M. Electrophilic Selenium, Selenocyclizations. In: Wirth T. (Ed). Topics in Current Chemistry: Organoselenium Chemistry: Modern Developments in Organic Synthesis (2000), Springer, Heidelberg 7-54
21. In: Back T.G. (Ed). Organoselenium Chemistry-A Pratical Approach (2000), Oxford University Press, New York, NY
22. Wirth T. Curr. Org. Chem. 10 (2006) 1893
23. Takada H., Nishibayashi Y., and Uemura S. J. Chem. Soc., Perkin Trans. 1 (1999) 1511
24. Nishibayashi Y., Srivastava S.K., Takada H., Fukuzawa S., and Uemura S. J. Chem. Soc., Chem. Commun. (1995) 2321
25. Fragale G., and Wirth T. Eur. J. Org. Chem. (1998) 1361
26. Deziel R., and Malefant E. J. Org. Chem. 60 (1995) 4660
27. Back T.G., Dyck B.P., and Nan S. Tetrahedron 55 (1999) 3191
28. Tiecco M., Testaferri L., Marini F., Sternativo S., Bagnoli L., Santi C., and Temperini A. Tetrahedron: Asymmetry 12 (2001) 1493
29. Tiecco M., Testaferri L., Marini F., Sternativo S., Santi C., Bagnoli L., and Temperini A. Tetrahedron: Asymmetry 12 (2001) 3053
30. Tiecco M., Testaferri L., Bagnoli L., Purgatorio V., Temperini A., Marini F., and Santi C. Tetrahedron: Asymmetry 12 (2001) 3297
31. Tiecco M., Testaferri L., Bagnoli L., Purgatorio V., Temperini A., Marini F., and Santi C. Tetrahedron: Asymmetry 15 (2004) 405
32. Tiecco M., Testaferri L., Bagnoli L., Terlizzi R., Temperini A., Marini F., Santi C., and Scarponi C. Tetrahedron: Asymmetry 15 (2004) 1949
33. Tiecco M., Testaferri L., Marini F., Sternativo S., Santi C., Bagnoli L., and Temperini A. Tetrahedron: Asymmetry 14 (2003) 1095
34. Tiecco M., Testaferri L., Marini F., Sternativo S., Santi C., Bagnoli L., and Temperini A. Tetrahedron: Asymmetry 14 (2003) 2651
35. Bernardi L., Bonini B.F., Comes-Franchini M., Fochi M., Mazzanti G., Ricci A., and Varchi G. Eur. J. Org. Chem. (2002) 2776
36. In: Paulmier C. (Ed). Selenium Reagents and Intermediates in Organic Synthesis (1986), Pergamon, Oxford
37. Krief A., Dumont W., Denis J.-N., Evrard G., and Norberg B. J. Chem. Soc., Chem. Commun. (1985) 569
38. Tiecco M., Testaferri L., Tingoli M., Chianelli D., and Bartoli D. Gazz. Chim. Ital. 117 (1987) 423
39. Krief A., Dumont W., and Denis J. J. Chem. Soc., Chem. Commun. (1985) 571
40. Copper M.A., and Ward D.A. Aust. J. Chem. 50 (1997) 181
41. Copper M.A., and Ward D.A. Tetrahedron Lett. 35 (1994) 5065
42. Tiecco M., Chianelli D., Testaferri L., Tingoli M., and Bartoli D. Tetrahedron 42 (1986) 4889
43. Tiecco M., Chianelli D., Tingoli M., and Testaferri L. Tetrahedron 42 (1986) 4897
44. Krief A., Dumont W., and De Mahieu A.F. Tetrahedron Lett. 29 (1988) 3265
45. Krief A., Dumont W., and De Mahieu A.F. Tetrahedron Lett. 29 (1988) 3269
46. Tiecco M., Testaferri L., Temperini A., Bagnoli L., Marini F., and Santi C. Chem. Eur. J. 10 (2004) 1752
47. Toshimitsu A., and Fuji H. Chem. Lett. (1992) 2017
48. Toshimitsu A., Hirosawa C., Tanimoto S., and Uemura S. Tetrahedron Lett. 28 (1992) 4017
49. Bartoli G., Bosco M., Dalpozzo R., Giuliani A., Marcantoni E., Mecozzi T., Sambri L., and Torregiani E. J. Org. Chem. 67 (2002) 9111
50. Chu W., Zhang J., Zeng C., Rothfuss J., Tu Z., Chu Y., Reichert D.E., Welch M.J., and Mach R.H. J. Med. Chem. 48 (2005) 7637
51. Ceccherelli P., Curini M., Epifano F., Marcotullio M.C., and Rosati O. J. Org. Chem. 60 (1995) 8412
52. McKennon M.J., and Meyers A.I. J. Org. Chem. 58 (1993) 3568
53. Kanth J.V.B., and Periasamy M. J. Org. Chem. 56 (1991) 5964
54. Bolognese A., Fierro O., Guarino D., Longobardo L., and Caputo R. Eur. J. Org. Chem. (2006) 169
55. Park S.H., Kang H.J., Ko S., Park S., and Chang S. Tetrahedron: Asymmetry 12 (2001) 2621
56. Bellis E., Vasilatou K., and Kokotos G. Synthesis 14 (2005) 2407
57. Afonso C.A. Synth. Commun. 28 (1998) 261