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Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin
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(a) Paris, J. M.; Barriere, J. C.; Smith, C.; Bost, P. E. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; pp 183-248.
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Williams, D.R.1
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11
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0032514515
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(f) Pattenden, G.; Plowright, A. T.; Tornos, J. A.; Ye, T. Tetrahedron Lett. 1998, 39, 6099-6102.
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(k) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597-5598.
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Forsyth, C.J.1
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Lee, C.S.4
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17
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85034150716
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-
The carbanion of 2 may be delocalized into the C=N π system
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The carbanion of 2 may be delocalized into the C=N π system.
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19
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0032578736
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(b) Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Pagel, M. Tetrahedron Lett. 1998, 39, 8023-8026.
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Williams, D.R.1
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21
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0001498230
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(d) Iddon, B. Heterocycles 1994, 37, 1321-1346.
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Iddon, B.1
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22
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0026707660
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For approaches developed in response to this difficulty see refs 7a,c and: (a) Gangloff, A. R.; Akermark, B.; Helquist, P. J. Org. Chem. 1992, 57, 4797-4799.
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Gangloff, A.R.1
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24
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0020604138
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(c) Nagao, Y.; Yamada, S.; Fujita, E. Tetrahedron Lett. 1983, 24, 2287-2290.
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Nagao, Y.1
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Fujita, E.3
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26
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0031597449
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See also: (b) Entwistle, D. A.; Jordan, S. I.; Montgomery, J.; Pattenden, G. Synthesis 1998, 603-612.
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Synthesis
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Entwistle, D.A.1
Jordan, S.I.2
Montgomery, J.3
Pattenden, G.4
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27
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0029886544
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(c) Garey, D.; Ramirez, M.; Gonzales, S.; Wertsching, A.; Tith, S.; Keefe, K.; Pena, M. R. J. Org. Chem. 1996, 61, 4853-4856.
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Tith, S.5
Keefe, K.6
Pena, M.R.7
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28
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0009766911
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(d) Bowie, J. H.; Donaghue, P. F.; Rodda, H. J.; Cooks R. G.; Williams, D. H. Org. Mass Spectrom. 1968, 1, 13-29.
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Rodda, H.J.3
Cooks, R.G.4
Williams, D.H.5
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29
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0041610595
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Dilithiated 3-methylthiophene-2-carboxylic acid has been reported to give a different distribution of regioisomers with alkyl bromides than with other electrophiles (acetone, methyl iodide, and deuterium oxide): Gould, N. P.; Lee, T.-J. J. Org. Chem. 1980, 45, 4530-4532.
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Gould, N.P.1
Lee, T.-J.2
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30
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85034128585
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note
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1H NMR to contain 6d as the only methylated product and ≤3% of the starting material 1d.
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31
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0000861392
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Knaus, G.; Meyers, A. I. J. Org. Chem. 1974, 39, 1192-1195. This study did not report the use of lithium diethylamide.
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Knaus, G.1
Meyers, A.I.2
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32
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0030877879
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See refs 5d,e and: (a) Celatka, C. A.; Liu, P.; Panek, J. S. Tetrahedron Lett. 1997, 38, 5449-5452.
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Celatka, C.A.1
Liu, P.2
Panek, J.S.3
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35
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85034137516
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The details of the synthesis of fragments 10 and 11 will be reported in due course
-
The details of the synthesis of fragments 10 and 11 will be reported in due course.
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-
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36
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85034150704
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note
-
1H NMR has allowed the observation of distinct intermediates consistent with 2 and 3 as well as their complete equilibration to 2. Analysis of the products 6 and 7 formed upon quenching these reactions suggests that ring alkylation of 2 is not occurring. For more details, see the Supporting Information.
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37
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0001426580
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This conclusion is supported by the results of Fraser et al., who have reported that the rate of proton exchange between amines and lithiated amides decreases with increasing steric bulk: Fraser, R. R.; Baignee, A.; Bresse, M.; Hata, K. Tetrahedron Lett. 1982, 23, 4195-4198.
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Fraser, R.R.1
Baignee, A.2
Bresse, M.3
Hata, K.4
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38
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85034133270
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It cannot be ruled out that the kinetic selectivity of lithium diethylamide favors the formation of 2
-
It cannot be ruled out that the kinetic selectivity of lithium diethylamide favors the formation of 2.
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-
-
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39
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85034138400
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1H NMR
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1H NMR.
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-
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40
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0000755015
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Levine, R.; Dimmig, D. A.; Kadunce, W. M. J. Org. Chem. 1974, 39, 3834-3837.
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Levine, R.1
Dimmig, D.A.2
Kadunce, W.M.3
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