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DOI: 10.1055/s-2004-81548
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Crackett, P.; Demont, E.; Eatherton, A.; Frampton, C. S.; Gilbert, J.; Kahn, I.; Redshaw, S.; Watson, W. Synlett 2004, DOI: 10.1055/s-2004-81548.
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Frampton, C.S.4
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(a) For an example of selective deprotonation of non-symmetrical ketones using a chiral amide base see: Sobukawa, M.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1990, 1, 295.
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33748630800
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and references therein
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Thomas, G.J.13
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12
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0033819390
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Use of propiolate trialkylester could have avoided obtaining this by-product but the large scale synthesis of these compounds was considered difficult. See for example: Baldwin, J. E.; Pritchard, G. J.; Rathmell, R. E. Synth. Commun. 2000, 30, 3833.
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Baldwin, J.E.1
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Rathmell, R.E.3
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13
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0026657406
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For the procedures used to synthesize 17 see: (a) Brimble, M. A.; Edmonds, M. K.; Williams, G. M. Tetrahedron 1992, 48, 6455. (b) Marshall, J. A. ; Andrews, R. C.; Lebioda, L. J. Org. Chem. 1987, 52, 2378.
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Brimble, M.A.1
Edmonds, M.K.2
Williams, G.M.3
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14
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0000197460
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For the procedures used to synthesize 17 see: (a) Brimble, M. A.; Edmonds, M. K.; Williams, G. M. Tetrahedron 1992, 48, 6455. (b) Marshall, J. A. ; Andrews, R. C.; Lebioda, L. J. Org. Chem. 1987, 52, 2378.
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Marshall, J.A.1
Andrews, R.C.2
Lebioda, L.3
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15
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0032566021
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This type of compound can be obtained by olefin metathesis but the high dilution of these reaction is not compatible with the scale of reaction envisioned in this synthesis, see: Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
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Ghosh, A.K.1
Cappiello, J.2
Shin, D.3
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16
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0027366768
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Emery, L.A.2
Stier, M.A.3
Suto, M.J.4
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18
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1642418004
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CCDC No. 217035 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the CCDC 12 Union Road Cambridge CB2 1EZ UK; fax:+44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk)
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19
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0001367782
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and references cited therein
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2 does not usually reduce ester. See Molander, G. A. Org. React. 1994, 46, 211-367; and references cited therein.
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Molander, G.A.1
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21
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1642416417
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An other approach was attempted using literature precedent, see: (a) Hanessian, S.; Haeil, P.; Rui-Yang, Y. Synlett 1997, 353. (b) Nicoll-Griffith,D. A.; Weiler, L. Tetrahedron 1991, 47, 2733.
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Hanessian, S.1
Haeil, P.2
Rui-Yang, Y.3
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22
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0026024344
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An other approach was attempted using literature precedent, see: (a) Hanessian, S.; Haeil, P.; Rui-Yang, Y. Synlett 1997, 353. (b) Nicoll-Griffith,D. A.; Weiler, L. Tetrahedron 1991, 47, 2733.
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Nicoll-Griffith, D.A.1
Weiler, L.2
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23
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0000763561
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N,N-Dibenzyl amine was considered to be a reasonable solution. For an excellent review on N,N-dibenzylamino compounds see: Reetz, M. T. Chem. Rev. 1999, 99, 1121.
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Reetz, M.T.1
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24
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1642332016
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note
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The reaction of 14 with oxazolidinone 4 was non-selective. Adduct 28 was obtained as a 1:1 mixture of trans-isomers.
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25
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1642328810
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note
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The direct reduction of allylic sulfone 28 gave a mixture of alkenes.
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