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For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
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For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
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For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
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Tetrahedron Lett.
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Brieden, W.2
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0042292102
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note
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A detailed discussion of the procedures that were followed for the assignment of the aldol-related stereochemical relationships is contained in the Supporting Information.
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13
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0042793054
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note
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Based on dielectric constants, it is not clear why the more polar diethyl ether (e = 4.3) is a better solvent than toluene (e = 2.4). However, ether was typically used because it provided the cleanest reaction mixtures.
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14
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0042793055
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note
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4 were also found to give extremely low levels of stereochemical induction.
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15
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0042793057
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note
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This observation has also been noted in the addition of enolsilanes to β-alkoxyaldehydes. See ref 3.
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16
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0025780257
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Buschmann, H.1
Scharf, H.-D.2
Hoffmann, N.3
Esser, P.4
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17
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0042793056
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note
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The optimal solvent for these reactions is diethyl ether. However, the reaction mixture is heterogeneous from the point of enolization until the quench.
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18
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0033575415
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Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Côté, B.; Dias. L. C.; Rajapakse, H.; Tyler, A. N. Tetrahedron 1999, 55, 8671-8726.
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Dias, L.C.5
Rajapakse, H.6
Tyler, A.N.7
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21
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0042292100
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note
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This reaction has been carried out by Dr. Kenneth J. McRae (Harvard University).
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26
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0037149036
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(e) Paterson, I.; Chen, D. Y. K.; Coster, M. J.; Acena, J. L.; Bach, J.; Gibson, K. R.; Keown, L. E.; Oballa, R. M.; Trieselmann, T.; Wallace, D. J.; Hodgson, A. P.; Norcross, R. D. Angew. Chem., Int. Ed. 2001, 40, 4055-4060.
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28
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Zukerman-Schpector, J.4
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36
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0042793050
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note
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In the aldol reaction reported by Panek (eq 23), the indicated configurations of the acetal centers in both reactant and product are currently in question. This reaction has been reinvestigated by Professor L. C. Dias (Universidade Estadual de Campinas, Instituto De Quimica-UNICAMP, Caixa Postal 6154 Campinas SPBRAZIL) who has kindly informed me of his results and of the indicated configuration reassignment.
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