Selectivity in the halohydroxylation of cyclohexadienediols

Tetrahedron

Volumn 63, Issue 19, 2007, Pages 4095-4107

  Carrera, Ignacio ^a   Brovetto, Margarita C ^a   Seoane, Gustavo ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOHEXANE DERIVATIVE;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; HYDROXYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TEMPERATURE DEPENDENCE;

EID: 34047157004     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.109     Document Type: Article

References (58)

1. Brovetto M., Schapiro V., Cavalli G., Padilla P., Sierra A., Seoane G., Suescun L., and Mariezcurrena R. New J. Chem. 23 (1999) 549
2. For recent reviews on the use of these chiral diols, see:. Johnson R.A. Org. React. 63 (2004) 117
3. Hudlicky T., González D., and Gibson D. Aldrichimica Acta 32 (1999) 35
4. Carrera I., Brovetto M., and Seoane G. Tetrahedron Lett. 47 (2006) 7849
5. Rodriguez J., and Dulcere J.-P. Synthesis (1993) 1177 and references cited therein
6. Schroeder M. Chem. Rev. 80 (1980) 187
7. Sharpless K. Angew. Chem., Int. Ed. 41 (2002) 2024
8. Ullmann's Encyclopedia of Industrial Chemistry. 6th ed. Electronic release (1998), Wiley-VCH, Weinheim, Germany
9. Chiappe C., and Ruasse M.-F. In: Rappoport Z. (Ed). The Chemistry of Dienes and Polyenes Vol. 2 (2000), J. Wiley and Sons, New York, NY 545-641 Chapter 7
10. Mislow B.K., and Hellman H.M. J. Am. Chem. Soc. 73 (1950) 244
11. Izawa K., Okuyama T., Sakagami T., and Fueno T. J. Am. Chem. Soc. 95 (1973) 6752
12. Heasley V.L., and Chamberlain P.H. J. Org. Chem. 35 (1970) 539
13. Shellhamer D.F., Heasley V.L., Foster J.E., Luttrull J.K., and Heasley G.E. J. Org. Chem. 42 (1977) 2141
14. Heasley G.E., and Bundy J.M. J. Org. Chem. 43 (1978) 2793
15. Nelson D.J., Cooper P.J., and Soundararajan R. J. Am. Chem. Soc. 111 (1989) 1414
16. Heasley G.E., Hayse D.C., McClung G.R., and Strickland D.K. J. Org. Chem. 41 (1976) 334
17. Dalton D.R., and Davis R.M. Tetrahedron Lett. 13 (1972) 1057
18. Nguyen B.V., York C., and Hudlicky T. Tetrahedron 53 (1997) 8807
19. Hudlicky T., Restrepo-Sanchez N., Kary P.D., and Jaramillo-Gomez L.M. Carbohydr. Res. 324 (2000) 200
20. Hudlicky T., Tian X., Konigsberger K., Maurya R., Rouden J., and Fan B. J. Am. Chem. Soc. 118 (1996) 10752
21. Banwell M.G., Haddad N., Hudlicky T., Nugent T.C., Mackay M.F., and Richards S.L. J. Chem. Soc., Perkin Trans. 1 (1997) 1779
22. Nugent T.C., and Hudlicky T. J. Org. Chem. 63 (1998) 510
23. Bedekar A.V., Nair K.B., and Soman R. Synth. Commun. 24 (1994) 2299
24. Mangoni L., Adinolfi M., Barone G., and Parrilli M. Tetrahedron Lett. 14 (1973) 4485
25. Campbell M.M., Sainbury M., and Yavarzadeh R. Tetrahedron 40 (1984) 5063
26. Smietana M., Gouverneur V., and Mioskowski C. Tetrahedron Lett. 41 (2000) 193
27. Hudlicky T., Nugent T.C., and Griffith W. J. Org. Chem. 59 (1994) 7944
28. Hudlicky T., Price J.D., Rulin F., and Tsunoda T. J. Am. Chem. Soc. 112 (1990) 9439
29. Dalton D.R., Dutta V.P., and Jones D.C. J. Am. Chem. Soc. 91 (1968) 5498
30. 1
31. Gibson D., Hensley M., Yoshika H., and Mabry R. Biochemistry 9 (1970) 1626
32. Hudlicky T., Luna H., Price J.D., and Rulin F. J. Org. Chem. 55 (1990) 4683
33. If benzyl alcohol is used as the solvent, the corresponding O-benzylated derivative of bromohydrin 23a is isolated as a single isomer in 60% yield.
34. Brovetto, M. Master's thesis, Universidad de la República, Uruguay, 1997;
35. A silyl derivative of 18, protected in C-1 as a thexylated silyl ether, gave only 8% isolated yield of the corresponding bromohydrin when submitted to NBS-mediated bromohydroxylation.
36. Sweeney J.B., Knight J.R., and Thobhani S. Tetrahedron 62 (2006) 11565
37. Ruasse M.-F., Lo Moro G., Galland B., Bianchi R., Chiappe C., and Bellucci G. J. Am. Chem. Soc. 119 (1997) 12492
38. Hudlicky T., Luna H., Barbieri G., and Kwart L.D. J. Am. Chem. Soc. 110 (1988) 4735
39. Halogeno-olefins have also been epoxidized by peroxyacids under harsher conditions. See:. Fonseca G., and Seoane G. Tetrahedron: Asymmetry 16 (2005) 1393
40. Mandel M., Hudlicky T., Kwart L.D., and Whited G.M. J. Org. Chem. 58 (1993) 2331
41. Kahn S.D., Pau C.F., Chamberlin A.R., and Hehre W.J. J. Am. Chem. Soc. 109 (1987) 650
42. Langstaff E., Hamanaka E., Neville G., and Moir R. Can. J. Chem. 45 (1967) 1907
43. Bannard R., Caselman A., and Hawkins L. Can. J. Chem. 43 (1965) 2398
44. Bellucci G., Berti G., Bianchini R., Ingrosso G., and Mastrorilli E. Gazz. Chim. Ital. 106 (1976) 955
45. Bellucci G., Berti G., Ingrosso G., and Mastrorilli E. Tetrahedron Lett. 14 (1973) 3911
46. Clark M.A., Goering J.L., and Ganem B. J. Org. Chem. 65 (2000) 4058
47. Thatcher G. In: Thatcher G. (Ed). The Anomeric Effect and Associated Stereoelectronic Effects. ACS Symposium Series 539 (1993), ACS, Washington, DC 6-25 Chapter 2
48. Wolfe S. Acc. Chem. Res. 5 (1972) 102
49. Traynham J.G., and Pascual O.S. Tetrahedron 7 (1959) 165
50. Dewar M., and Thiel W. J. Am. Chem. Soc. 99 (1977) 2338
51. Davis L.P., et al. J. Comput. Chem. 2 (1981) 433
52. Dewar M., McKee M., and Rzepa H. J. Am. Chem. Soc. 100 (1978) 3607
53. Dewar M., Zoebisch E., and Healy E. J. Am. Chem. Soc. 107 (1985) 3902
54. Dewar M., and Reynolds C. J. Comput. Chem. 2 (1986) 140
55. Dewar M., and Jie C. J. Mol. Struct. (Theochem) 187 (1989) 1
56. Shellhamer D., Allen J., Allen R., Gleason D., Schlosser C., Powers B., Probst J., Rhodes M., Ryan A., Titterington P., Vaughan G., and Heasley V. J. Org. Chem. 68 (2003) 3932
57. Heasley V., Holstein III L., Moreland R., Rosbrugh Jr. J., and Shellhamer D. J. Chem. Soc., Perkin Trans. 2 (1991) 1271
58. Gene E., Heasley G.E., Smith D.A., Smith J.N., Heasley V.L., and Shellhamer D.F. J. Org. Chem. 45 (1980) 5206