-
4
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-
33748153822
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See, for instance:
-
-
-
-
6
-
-
1542535886
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Matsuhita M., Nagoaka Y., Hioki H., Fukuyama Y., and Kodama M. Chem. Lett. (1996) 1039-1040
-
(1996)
Chem. Lett.
, pp. 1039-1040
-
-
Matsuhita, M.1
Nagoaka, Y.2
Hioki, H.3
Fukuyama, Y.4
Kodama, M.5
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7
-
-
33748139041
-
-
An additional problem arises when G=vinyl because the [1,4]-shift of the group R competes with the [1,2]-rearrangement giving an aldehyde. See, for instance:
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-
-
-
11
-
-
33748171678
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-
See, for instance:
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-
-
-
13
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33748159340
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-
This type of α-oxygenated organolithium compounds have been used in synthetic organic chemistry by reaction with different carbonyl compounds under Barbier conditions (performing the lithiation in the presence of the electrophile); for a review, see:
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-
-
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16
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33748206904
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See, Ref. 6;
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-
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17
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33748153821
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See also:
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-
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25
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33748179456
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For reviews, see:
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-
-
-
28
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0034904455
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-
Yus M. Synlett (2001) 1197-1205
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(2001)
Synlett
, pp. 1197-1205
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-
Yus, M.1
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31
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-
33748199260
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-
Rappoport Z., and Marek I. (Eds), Wiley, Chichester, UK Part 2, Chapter 11
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Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), Wiley, Chichester, UK Part 2, Chapter 11
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(2004)
The Chemistry of Organolithium Compounds
, vol.1
-
-
Yus, M.1
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32
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33748203787
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For mechanistic studies, see:
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-
-
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38
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33748136143
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For a polymer supported arene-catalysed version of this reaction, see:
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-
-
-
45
-
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33748197940
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Ring opening of heterocycles:
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-
-
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47
-
-
40749138993
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-
Attanasi O.A., and Spinelli D. (Eds), Italian Society of Chemistry, Rome
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Yus M., and Foubelo F. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems Vol. 6 (2002), Italian Society of Chemistry, Rome 136-171
-
(2002)
Targets in Heterocyclic Systems
, vol.6
, pp. 136-171
-
-
Yus, M.1
Foubelo, F.2
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49
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33748190882
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-
Preparation of organolithium compounds from non-halogenated materials:
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-
-
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51
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33748208864
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Generation of dilithium synthons:
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55
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33748171202
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Activation of metals:
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62
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33748194782
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See, for instance:
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-
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-
65
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2542447275
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-
We have observed this behaviour in other cases: due to the low density of lithium metal, at 1 mmol scale and with mechanical stirring, a part of the metal remains on the wall of the flask, so an excess (ca. 1:7 molar ratio) should be used, this problem disappearing at higher scale. See, for instance: (Corrigendum: Synthesis 2004, 1720)
-
We have observed this behaviour in other cases: due to the low density of lithium metal, at 1 mmol scale and with mechanical stirring, a part of the metal remains on the wall of the flask, so an excess (ca. 1:7 molar ratio) should be used, this problem disappearing at higher scale. See, for instance:. Yus M., Moreno B., and Foubelo F. Synthesis (2004) 1115-1118 (Corrigendum: Synthesis 2004, 1720)
-
(2004)
Synthesis
, pp. 1115-1118
-
-
Yus, M.1
Moreno, B.2
Foubelo, F.3
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68
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33748150577
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-
note
-
Compound 1n was thermically very unstable and was obtained after distillation in ca. 70% purity, containing ca. 30% of benzyl chloride. This mixture was used directly for the lithiation step, the corresponding given yield for the product 2n (Table 1, entry 14) being based on the mentioned proportion of compound 1n.
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-
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72
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33748209304
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Chem. Abstr. 61 (1964) 92113
-
(1964)
Chem. Abstr.
, vol.61
, pp. 92113
-
-
-
73
-
-
33748203133
-
-
Undheim, K.; Benneche, T. Eur. Pat. 160573 A2 19851106, 1985;
-
-
-
-
74
-
-
33748194345
-
-
Chem. Abstr. 104 (1986) 129922
-
(1986)
Chem. Abstr.
, vol.104
, pp. 129922
-
-
-
76
-
-
0021682112
-
-
Bedford C.D., Harris III R.N., Howd R.A., Miller A., Nolen III H.W., and Kenley R.A. J. Med. Chem. (1984) 1431-1438
-
(1984)
J. Med. Chem.
, pp. 1431-1438
-
-
Bedford, C.D.1
Harris III, R.N.2
Howd, R.A.3
Miller, A.4
Nolen III, H.W.5
Kenley, R.A.6
-
78
-
-
9344245165
-
-
Knoepfel T.F., Aschwanden P., Ichikawa T., Watanabe T., and Carreira E.M. Angew. Chem., Int. Ed. 43 (2004) 5971-5973
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 5971-5973
-
-
Knoepfel, T.F.1
Aschwanden, P.2
Ichikawa, T.3
Watanabe, T.4
Carreira, E.M.5
-
80
-
-
28144463966
-
-
Hardcastle I.R., Cockcroft X., Curtin N.J., El-Murr M.D., Leahy J.J.J., Stockley M., Golding B.T., Rigoreau L., Richardson C., Smith G.C.M., and Griffin R.J. J. Med. Chem. 48 (2005) 7829-7846
-
(2005)
J. Med. Chem.
, vol.48
, pp. 7829-7846
-
-
Hardcastle, I.R.1
Cockcroft, X.2
Curtin, N.J.3
El-Murr, M.D.4
Leahy, J.J.J.5
Stockley, M.6
Golding, B.T.7
Rigoreau, L.8
Richardson, C.9
Smith, G.C.M.10
Griffin, R.J.11
-
82
-
-
85027846426
-
-
Zhao M.M., Li J., Mano E., Song Z.J., and Tschaen D.M. Org. Synth. 81 (2005) 195-203
-
(2005)
Org. Synth.
, vol.81
, pp. 195-203
-
-
Zhao, M.M.1
Li, J.2
Mano, E.3
Song, Z.J.4
Tschaen, D.M.5
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