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(b) Andrey, O.; Landais, Y.; Planchenault, D. Tetrahedron Lett., 1993, 34, 2927-2930;
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(c) Andrey, O.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron, 1995, 51, 12083-12096;
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(h) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L., Tetrahedron, preceding communication in this issue;
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2. For other asymmetric access to α-silylcarbonyl compounds, see : (a) Enders, D.; Nakai, S. Helv. Chim. Acta, 1990, 73, 1833-1836;
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(c) Bhushan, V.; Lohray, B.B.; Enders, D. Tetrahedron Lett., 1993, 34, 5067-5070;
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(e) Le Bideau, F.; Gilloir, F.; Nilsson, Y.; Aubert, C.; Malacria, M. Ibid., 1995, 36, 1641-1644;
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Le Bideau, F.1
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(f) Paquette, L.A.; Maynard, J.D.; Ra, C.S.; Hoppe, M. J. Org. Chem., 1989, 54, 1408-1418;
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0011483955
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(g) Paquette, L.A.; Gilday, J.P.; Ra, C.S.; Hoppe, M. Ibid., 1988, 53, 704-706;
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Paquette, L.A.1
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0000723265
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(h) Gilday, J.P.; Gallucci, J.C.; Paquette, L.A. Ibid., 1989, 54, 1399-1408;
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Gilday, J.P.1
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0028898314
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(i) Le Bideau, F.; Aubert, C.; Malacria, M. Tetrahedron : Asymmetry, 1995, 6, 697-700;
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Le Bideau, F.1
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(j) Le Bideau, F.; Gilloir, F.; Nilsson, Y.; Aubert, C.; Malacria, M. Tetrahedron, 1996, 52, 7487-7510;
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Le Bideau, F.1
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33748916441
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(k) Enders, E; Lohray, B.B.; Burkamp, F.; Bhushan, V.; Hett, R. Liebigs. Ann. Chem., 1996, 189-200.
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Enders, E.1
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21
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33847799798
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3. Ireland, R.E.; Muller, R.H.; Willard, A.K. J. Am. Chem. Soc., 1976, 98, 2868-2877.
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Ireland, R.E.1
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22
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84987568818
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4. 8a-b were prepared according to reported procedures : (a) Doyle, M.P.; Protopopova, M.N.; Brandes, B.D.; Davies, H.M.L.; Huby, N.J.S.; Whitesell, J.K. Synlett, 1993, 151-153;
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Doyle, M.P.1
Protopopova, M.N.2
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Davies, H.M.L.4
Huby, N.J.S.5
Whitesell, J.K.6
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23
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0025358489
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(b) Doyle, M.P.; Bagheri, V.; Wandless, T.J.; Harn, N.K.; Brinker, D.A.; Eagle, C.T.; Loh, K.-L. J. Am. Chem. Soc., 1990, 112, 1906-1912.
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Eagle, C.T.6
Loh, K.-L.7
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24
-
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0001644203
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5. 7a-c are commercially available. 7d was prepared by addition of the Grignard of 1-bromonaphtalene to (+)-camphor following a reported protocol : Somfai, P.; Tanner, D.; Olsson, T. Tetrahedron, 1985, 41, 5973-5980.
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Somfai, P.1
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25
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0000709206
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and references cited therein
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33947335944
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Balwin, J.E.1
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28
-
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0011436472
-
-
note
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11 might be invoked here. (equation presented)
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29
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0000184426
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10. Doyle, M.P.; Dorow, R.L.; Terpstra, J.W.; Rodenhouse, R.A. J. Org. Chem., 1985, 50, 1663-1666.
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32
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0027939290
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13. (a) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett., 1994, 35, 9549-9552;
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Landais, Y.1
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34
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0027978020
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(c) Aller, E.; Cox, G.G.; Miller, D.J.; Moody, C.J. Tetrahedron Lett., 1994, 35, 5949-5952;
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Aller, E.1
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35
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0030025340
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(d) Ferris, L.; Haigh, D.; Moody, C.J. Ibid., 1996, 37, 107-110.
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Ferris, L.1
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0000177311
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14. For a recent synthesis of α-diazoesters, see : Taber, D.F.; You, K.; Song, Y. J. Org. Chem., 1995, 60, 1093-1094.
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Taber, D.F.1
You, K.2
Song, Y.3
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37
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0001068547
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15. Chiral auxiliaries 16d-e are commercially available. 16b-c were prepared from (1S)-(+)-camphorquinone, following a reported procedure : Oppolzer, W.; Chapuis, C.; Dao, G.M.; Reichlin, D.; Godel, T. Tetrahedron Lett., 1982, 23, 4781-4784.
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0001285938
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(b) Ort, O. Org. Synth., 1987, 65, 203-214.
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0026012209
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17. (a) Davies, H.M.L.; Saikali, E.; Young, W.B. J. Org. Chem., 1991, 56, 5696-5700;
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Davies, H.M.L.1
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41
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0000942993
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(b) Davies, H.M.L.; McAfee, M.J.; Oldenburg, C.E.M. Ibid., 1989, 54, 930-936.
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Davies, H.M.L.1
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43
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0000234509
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19. (a) Doyle, M.P.; Westrum, L.J.; Wendelmoed, N.E.W.; See, M.M.; Boone, W.P.; Bagheri, V.; Pearson, M.M. J. Am. Chem. Soc., 1993, 115, 958-964;
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Doyle, M.P.1
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Wendelmoed, N.E.W.3
See, M.M.4
Boone, W.P.5
Bagheri, V.6
Pearson, M.M.7
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45
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0028272257
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20. For a similar behaviour found in rhodium-carbene insertion into the O-H bond, see : Cox, G.G.; Haigh, D.; Hindley, R.M.; Miller, D.J.; Moody, C.J. Tetrahedron Lett., 1994, 35, 3139-3142.
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Cox, G.G.1
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Miller, D.J.4
Moody, C.J.5
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46
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0001782321
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21. For reviews on the use of the silicon group as a masked hydroxy group, see : (a) Fleming, I. Chemtracts, Org. Chem., 1996, 9, 1-64;
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Fleming, I.1
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47
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0030007621
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21a,b but was not performed in our case due to the low diastereosetectivity of the insertion process.
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Jones, G.R.1
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0017136359
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22. 24a is commercially available (Fluka). 24b : Mori, K. Tetrahedron, 1976, 32, 1101-1106; 24c : Bergstein, W.; Kleemann, A.; Martens, J. Synthesis, 1981, 76-78.
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Mori, K.1
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49
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85077687113
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22. 24a is commercially available (Fluka). 24b : Mori, K. Tetrahedron, 1976, 32, 1101-1106; 24c : Bergstein, W.; Kleemann, A.; Martens, J. Synthesis, 1981, 76-78.
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Bergstein, W.1
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50
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0011393286
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23. Acetals were prepared from die 1,2-diols in the presence of benzaldehyde and a catalytic amount of p-TsOH. The enantiomeric excesses were measured following Eliel's procedure : Eliel, E.L.; Ko, K.-Y. Tetrahedron Lett., 1983, 34, 3547-3550.
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0000202165
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Olive, J.L.4
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53
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0011437578
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Reduction and C-Si bond oxidation of 27a-b gave diol 24a and 1-phenylethane-1,2-diol respectively.
-
26. Reduction and C-Si bond oxidation of 27a-b gave diol 24a and 1-phenylethane-1,2-diol respectively.
-
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54
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0000698918
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27. Baum, J.S.; Shook, D.A.; Davies, H.M.L.; Smith, H.D. Synth. Commun., 1987, 17, 1709-1716.
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