Microwave-assisted epoxidation of hindered homoallylic alcohols using VO(acac) 2: Application to polypropionate synthesis

Tetrahedron

Volumn 60, Issue 45, 2004, Pages 10245-10251

  Torres, Gerardo ^a   Torres, Wildeliz ^a   Prieto, José A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

Epoxidation; Homoallylic alcohols; Microwave synthesis; Polypropinate synthesis

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CIS ISOMER; DIASTEREOISOMER; EPOXIDATION; MICROWAVE IRRADIATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SOLVENT EFFECT; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; TECHNIQUE; TRANS ISOMER;

EID: 4644341193     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.095     Document Type: Article

References (45)

1. E.J. Corey, and T. Hase Tetrahedron Lett. 20 1979 335
2. B.H. Lipshutz, and J. Kozlowski J. Org. Chem. 49 1984 1147
3. B.H. Lipshutz, and J.C. Barton J. Org. Chem. 53 1988 4495
4. P. Mohr Tetrahedron Lett. 33 1992 2455
5. S.A. Burova, and F.E. McDonald J. Am. Chem. Soc. 124 2002 8188
6. H.J. Martin, M. Drescher, and J. Mulzer Angew. Chem., Int. Ed. 39 2000 581
7. Z. Wang, and S.L. Schreiber Tetrahedron Lett. 31 1990 312
8. T. Okachi, N. Murai, and M. Onaka Org. Lett. 5 2003 85
9. E.R. Bryant, and K.B. Sharpless J. Org. Chem. 49 1984 3707
10. S. Ikegami, T. Katsuki, and M. Yamaguchi Chem. Lett. 1987 83
11. G. Guanti, L. Bamfi,. Narisano, and S. Thea Tetrahedron Lett. 32 1991 6943
12. J.K. Karjalainen, O.E.O. Hormi, and D.C. Sherrington Tetrahedron: Asymmetry 9 1998 3895
13. G. Cardillo, and M. Orena Tetrahedron 46 1990 3321
14. A. Bongini, G. Cardillo, M. Orena, G. Porzi, and S. Sandri J. Org. Chem. 47 1982 4626
15. P.A. Bartlett, J.D. Meadows, E.G. Brown, A. Morimoto, and K.K. Junstedt J. Org. Chem. 47 1982 4013
16. P.A. Bartlett, and J. Myerson J. Am. Chem. Soc. 100 1978 3950
17. R.C. Michaelson, and K.B. Sharpless J. Am. Chem. Soc. 95 1973 6136
18. E.D. Mihelich, K. Daniels, and D.J. Eickhoff J. Am. Chem. Soc. 103 1981 7690
19. E.D. Mihelich Tetrahedron Lett. 20 1979 4729
20. K.B. Sharpless, and T.R. Verhoeven Aldrichim. Acta 12 1979 63
21. R. Tirado, and J.A. Prieto J. Org. Chem. 58 1993 5666
22. D.O. Arbelo, L. Castro-Rosario, and J.A. Prieto Synth. Commun. 33 2003 3211
23. D.O. Arbelo, and J.A. Prieto Tetrahedron Lett. 43 2002 4111
24. L. Perreux, and A. Loupy Tetrahedron 57 2001 9199
25. A. Loupy, L. Perreux, M. Liagre, K. Burle, and M. Moneuse Pure Appl. Chem. 73 2001 161
26. P. Lidstrom, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
27. C. Gabriel, S. Gabriel, E.H. Grant, B.S. Halstead, and M.P. Mingos Chem. Soc. Rev. 27 1998 213
28. S. Caddick Tetrahedron 51 1995 10403
29. S. Deshayes, M. Liagre, A. Loupy, J.L. Luche, and A. Petti Tetrahedron 55 1999 10851
30. A.A. dos Santos, E.P. Wendler, F. de A. Marques, and F. Simonelli Lett. Org. Chem. 1 2004 47
31. L. Palombi, F. Bonadies, and A. Scettri Tetrahedron 53 1997 15867
32. U.R. Pillai, E. Sahle-Demessie, and R.S. Varma Tetrahedron Lett. 43 2002 2909
33. J. Fawcett, G.A. Griffith, J.M. Percy, and E. Uneyama Org. Lett. 6 2004 1277
34. A. Sharifi, M. Bolourtchian, and F. Mohsenzadeh J. Chem. Res. 1998 668
35. The 2-methyl-3,4-epoxy alcohols 11a-d were prepared by the diethylpropynylalane cleavage of the cis or trans TIPS-protected 2,3-epoxy-1-butanols followed by a cis or trans reduction of the homopropargylic alcohols (Ref. 5).
36. S. Chandrasekhar, Ch. Narasihmulu, V. Jagadeshwar, and K.V. Reddy Tetrahedron Lett. 44 2003 3629
37. N.E. Leadbeater, and H.M. Torrenius J. Org. Chem. 67 2002 3145
38. E. Van der Eycken, P. Appukkuttan, W. De Borggraeve, W. Dehaen, D. Dalliger, and C.O. Kappe J. Org. Chem. 67 2002 7904
39. A. Lattanzi, and N.E. Leadbeater Org. Lett. 4 2002 1519
40. Corrections for the borosilicate glass vessel, which is known to transfer some microwave energy was not made S. Garbacia, B. Desai, O. Levastre, and C.O. Kappe J. Org. Chem. 68 2003 9136
41. cis Alkene diols 12 and 14 were prepared from the corresponding diethylalkynylalane cleavage of epoxide 8c syn, followed by the Pd/C, quinoline hydrogenation of the resulting alkynes. Alkenol 16 was similarly prepared from epoxide 13 (Ref. 5).
42. K. Rinehart, M.L. Maheshwari, F.J. Antosz, H.H. Mathur, K. Sasaki, and R.J. Schacht J. Am. Chem. Soc. 93 1971 6273
43. K.L. Rinehart, F.J. Antosz, K. Sasaki, P.K. Martin, M.L. Maheshwari, F. Reussre, H.L. Li, D. Moran, and P.F. Wiley Biochemistry 13 1974 861
44. M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, M. Miyazawa, and H. Irie Chem. Commun. 1996 1027
45. S.D. Rychnovsky, B. Rogers, and G. Yang J. Org. Chem. 58 1993 3511