Study on the stereochemical control of dihydroxylation of vinyl epoxides and their derivatives

Tetrahedron

Volumn 68, Issue 14, 2012, Pages 2984-2992

  Righi, Giuliana ^a   Mandic', Emanuela ^b   Naponiello, Gaia Clara Mercedes ^b   Bovicelli, Paolo ^a   Tirotta, Ilaria ^b  

^a CNR   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Azidoalcohols; Bromohydrins; Dihydroxylation; Vinyl aziridines; Vinyl epoxides

Indexed keywords

ALCOHOL; AZIDE; AZIRIDINE DERIVATIVE; BROMINE DERIVATIVE; EPOXIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL EPOXIDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; DIASTEREOISOMER; DIHYDROXYLATION; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84858706515     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.029     Document Type: Article

References (39)

1. R. Pulz, W. Schade, and H.-U. Reissing Synlett 2003 405 407
2. S.C. Bergmeier Tetrahedron 56 2000 2561 2576
3. R. Polt, D. Sames, and J. Chruma J. Org. Chem. 64 1999 6147 6158
4. P. Righi, E. Marotta, and G. Rosini Chem. - Eur. J. 4 1998 2501 2508
5. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, and A. Restelli Helv. Chim. Acta 68 1985 1217 1225
6. Y. Ichikawa, Y. Igarashi, M. Ichikawa, and Y. Suhara J. Am. Chem. Soc. 120 1998 3007 3018
7. N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645 1680
8. K. Afarinkia, and A. Bahar Tetrahedron: Asymmetry 16 2005 1239 1287
9. J. Liao, J. Tao, G. Lin, and D. Liu Tetrahedron 61 2005 4715 4733
10. P.M. Koshinen, and A.M.P. Koshinen Synthesis 1998 1075 1091
11. Z. Liu, B. Wang, L. Zhao, Y. Li, H. Shao, H. Yi, X. You, and Z. Li Bioorg. Med. Chem. Lett. 17 2007 4851 4854
12. T.M. Altamore, P.J. Duggan, and G.Y. Krippner Bioorg. Med. Chem. 14 2006 1126 1133
13. T. Masuda, S. Shibuya, M. Arai, S. Yoshida, T. Tomozawa, A. Ohno, M. Yamashita, and T. Honda Bioorg. Med. Chem. Lett. 13 2003 669 673
14. G. Righi, S. Ciambrone, C. D'Achille, A. Leonelli, and C. Bonini Tetrahedron 62 2006 11821 11826
15. G. Righi, S. Ciambrone, and C. Bonini Synth. Commun. 36 2006 1157 1165
16. G. Righi, S. Ciambrone, and C. Bonini Bioorg. Med. Chem. 16 2008 902 908
17. G. Righi, A. Ferrara, A. Mari, and P. Bovicelli Synth. Commun. 40 2010 1650 1657
18. G. Righi, P. Bovicelli, R. Antonioletti, and E. Fazzolari Tetrahedron Lett. 41 2000 9315 9318
19. G. Righi, P. Bovicelli, and C. Potini Tetrahedron Lett. 43 2002 5867 5869
20. G. Righi, L. Salvati Manni, P. Bovicelli, and R. Pelagalli Tetrahedron Lett. 52 2011 3895 3896
21. Righi, G.; Marucci, C.; Bovicelli, P.; Tirotta, I. Synthesis, submitted for publication.
22. H.C. Kolb, M.S. Van Nieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 2547
23. Y. Kishi, J.K. Cha, and W.J. Christ Tetrahedron 40 1984 2247 2255
24. K.B. Sharpless, H.C. Kolb, and P.G. Anderson J. Am. Chem. Soc. 116 1994 1270 1278
25. S.A. Hermitage, A. Murphy, P. Nielsen, and M.R. Stanley Tetrahedron 54 1998 13185 13202
26. N. Kim, J. Choi, and J. Cha J. Org. Chem. 58 1993 7096 7099
27. J.S. Yadav, A. Raju, P. Rao, and G. Rajaiah Tetrahedron: Asymmetry 16 2005 3283 3290
28. E. Moran, J. Tellew, Z. Zhao, and E. Armstrong J. Org. Chem. 58 1993 7848 7859
29. J. Legters, L. Thijs, and B. Zwanemburg Recl. Trav. Chim. Pays-Bas 111 1992 1 15
30. S.D. Rychnovsky, B. Rogers, and G. Yang J. Org. Chem. 58 1993 3511 3515
31. W. Adam, and B. Nestler J. Am. Chem. Soc. 115 1993 7226 7236
32. E.D. Miheclich Tetrahedron Lett. 20 1979 4729 4732
33. G.I. Hwang, J.H. Chung, and W.K. Lee J. Org. Chem. 61 1996 6183 6188
34. J.M. Andres, N. de Elena, R. Pedrosa, and A. Pretz-Encavo Tetrahedron 55 1999 14137 14144
35. Y. Gao, J.M. Klunder, R.M. Hanson, H. Masamune, S.Y. Ko, and K.B. Sharpless J.Am. Chem. Soc. 109 1987 5765 5779
36. A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, and G. Piancatelli J. Org. Chem. 62 1997 6974 6977
37. G. Righi, A. Chionne, and C. Bonini Eur. J. Org. Chem. 18 2000 3127 3132
38. M. Miyashita, T. Mizutani, G. Tadano, Y. Iwata, M. Miyazawa, and K. Tanino Angew. Chem., Int. Ed. 44 2005 5094 5097
39. G. Righi, P. Bovicelli, M. Barontini, and I. Tirotta Green Chem. 14 2012 495 502