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1
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0000449913
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For reviews, see:
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For reviews, see: Martin S.F. Tetrahedron. 36:1980;419-460.
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Martin, S.F.1
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0001521888
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Fuji K. Chem. Rev. 93:1993;2037-2066.
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Fuji, K.1
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5
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84970550621
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The only reaction reported to date is that using organoaluminum reagents, see:
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The only reaction reported to date is that using organoaluminum reagents, see: Hamilton R.J., Mander L.N. Aust. J. Chem. 44:1991;927-938.
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Aust. J. Chem.
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Hamilton, R.J.1
Mander, L.N.2
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7
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0030981561
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Balasubramaniam R.P., Moss D.K., Wyatt J.K., Spence J.D., Gee A., Nantz M.H. Tetrahedron. 53:1997;7429-7444.
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Balasubramaniam, R.P.1
Moss, D.K.2
Wyatt, J.K.3
Spence, J.D.4
Gee, A.5
Nantz, M.H.6
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12
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0000957327
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For recent examples, see:
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For recent examples, see: Shimazaki M., Hara H., Suzuki K., Tsuchihashi G. Tetrahedron Lett. 28:1987;5891-5894.
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Shimazaki, M.1
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15
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0002447983
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Okada K., Katsura T., Tanino H., Kakoi H., Inoue S. Chem. Lett. 1994;157-160.
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Okada, K.1
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Inoue, S.5
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17
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8544276578
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Kita Y., Kitagaki S., Yoshida Y., Mihara S., Fang D.F., Kondo M., Okamoto S., Imai R., Akai S., Fujioka H. J. Org. Chem. 62:1997;4991-4997.
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Kita, Y.1
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Yoshida, Y.3
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Fang, D.F.5
Kondo, M.6
Okamoto, S.7
Imai, R.8
Akai, S.9
Fujioka, H.10
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19
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0035966223
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Kita Y., Furukawa A., Futamura J., Ueda K., Sawama Y., Hamamoto H., Fujioka H. J. Org. Chem. 66:2001;8779-8786.
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Kita, Y.1
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37049085296
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Tanaka T., Inoue T., Kamei K., Murakami K., Iwata C. J. Chem. Soc., Chem. Commun. 1990;906-908.
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Tanaka, T.1
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21
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0003780608
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For the epoxide cleavage at the allylic or benzylic position by titanium reagents prepared by chlorotitanium triisopropoxide, see: Berlin: Springer. pp. 218-219
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For the epoxide cleavage at the allylic or benzylic position by titanium reagents prepared by chlorotitanium triisopropoxide, see: Reetz M.T. Organotitanium Reagents in Organic Synthesis. 1986;Springer, Berlin. pp. 218-219.
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Reetz, M.T.1
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23
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0001615493
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Stereoselective reactions of cyclic epoxides such as substituted cyclohexene oxides with a titanium reagent were already reported, see Refs. [5] and [6b]. See also
-
Stereoselective reactions of cyclic epoxides such as substituted cyclohexene oxides with a titanium reagent were already reported, see Refs. [5] and [6b]. See also, Blandy C., Choukroun R., Gervais D. Tetrahedron Lett. 24:1983;4189-4192.
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Blandy, C.1
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Gervais, D.3
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26
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33845378115
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For titanium-mediated stereospecific ring-opening reactions of 2,3-epoxy alcohol derivatives, see:
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For titanium-mediated stereospecific ring-opening reactions of 2,3-epoxy alcohol derivatives, see: Caron M., Sharpless K.B. J. Org. Chem. 50:1985;1557-1560.
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Caron, M.1
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0025985752
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Canas M., Poch M., Verdaguer X., Moyano A., Pericás M.A., Riera A. Tetrahedron Lett. 32:1991;6931-6934.
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Canas, M.1
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Moyano, A.4
Pericás, M.A.5
Riera, A.6
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33
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33845374299
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For the reaction with 3-unsubstituted 2,3-epoxy alcohol derivatives, see (h):
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For the reaction with 3-unsubstituted 2,3-epoxy alcohol derivatives, see (h): Ko S.Y., Sharpless K.B. J. Org. Chem. 51:1986;5413-5415.
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Ko, S.Y.1
Sharpless, K.B.2
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34
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0007312102
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For titanium-mediated stereospecific ring-opening reactions of other acyclic epoxides, see:
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For titanium-mediated stereospecific ring-opening reactions of other acyclic epoxides, see: Sutowardoyo K., Emziane M., Sinou D. Tetrahedron Lett. 30:1989;4673-4676.
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Sutowardoyo, K.1
Emziane, M.2
Sinou, D.3
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18844410382
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Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., Sharpless K.B. J. Am. Chem. Soc. 109:1987;5765-5780.
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Gao, Y.1
Hanson, R.M.2
Klunder, J.M.3
Ko, S.Y.4
Masamune, H.5
Sharpless, K.B.6
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39
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0001713826
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Suzuki T., Saimoto H., Tomioka H., Oshima K., Nozaki H. Tetrahedron Lett. 23:1982;3597-3600.
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Suzuki, T.1
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0012550127
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Ahn K.H., Kim J.S., Jin C.S., Kang D.H., Han D.S., Shin Y.S., Kim D.H. Synlett. 1992;306-308.
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Ahn, K.H.1
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Kang, D.H.4
Han, D.S.5
Shin, Y.S.6
Kim, D.H.7
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44
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0037428006
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Diethylaluminum azide-mediated anti selective ring-opening reaction of 3,3-disubstituted 2,3-epoxy alcohols to give azidohydrins was recently reported, see (f):
-
Diethylaluminum azide-mediated anti selective ring-opening reaction of 3,3-disubstituted 2,3-epoxy alcohols to give azidohydrins was recently reported, see (f): Davis C.E., Bailey J.L., Lockner J.W., Coates R.M. J. Org. Chem. 68:2003;75-82.
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J. Org. Chem.
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Davis, C.E.1
Bailey, J.L.2
Lockner, J.W.3
Coates, R.M.4
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46
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0035939140
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Martín R., Islas G., Moyano A., Pericàs M.A., Riera A. Tetrahedron. 57:2001;6367-6374.
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Martín, R.1
Islas, G.2
Moyano, A.3
Pericàs, M.A.4
Riera, A.5
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48
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0038732511
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For a recent theoretical study, see:
-
For a recent theoretical study, see: Infante I., Bonini C., Lelj F., Righi G. J. Org. Chem. 68:2003;3773-3780.
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Infante, I.1
Bonini, C.2
Lelj, F.3
Righi, G.4
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49
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85030910262
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Halohydrin is one of the representative side products irrespective of the Grignard reagent used, the stereochemistry of which is not determined. No regioisomer of the allylated product was detected in the reaction mixture
-
Halohydrin is one of the representative side products irrespective of the Grignard reagent used, the stereochemistry of which is not determined. No regioisomer of the allylated product was detected in the reaction mixture.
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50
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85030904429
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note
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The stereochemistry of 8 was determined by NOE analysis of the corresponding lactone, which was obtained by ozonolysis followed by oxidation.
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51
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85030900543
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4. After purification by silica gel chromatography, 1,3-diol having a chiral quaternary carbon center was obtained
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4. After purification by silica gel chromatography, 1,3-diol having a chiral quaternary carbon center was obtained.
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