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Banwell, M.G.1
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Smith, J.A.4
Hamel, E.5
Verdier-Pinard, P.6
-
3
-
-
0032795262
-
-
We prefer to describe these conversions as Michael addition reactions rather than Friedel-Crafts processes since the pyrrole nitrogen can also add to an acrylate tethered through C2 of this five-membered heterocycle (see, for example, M. G. Banwell, A. M. Bray, A. C. Willis and D. J. Wong, New J. Chem., 1999, 23, 687).
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Banwell, M.G.1
Bray, A.M.2
Willis, A.C.3
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4
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25544436935
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and references cited therein
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See, for example, R. Lueoend and R. Neier, Helv. Chim. Acta, 1991, 74, 91 and references cited therein.
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Helv. Chim. Acta
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Lueoend, R.1
Neier, R.2
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5
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0023883293
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(-)-8-Phenylmenthyl dimethyl phosphonoacetate (see H. J. Gais, G. Schmiedl, W. A. Ball, J. Bund, G. Hellmann and I. Erdelmeier, Tetrahedron Lett., 1988, 29, 1773) was used for the conversion 9→10 whilst commercially available trimethyl phosphonoacetate was used for the conversion 9→11.
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Gais, H.J.1
Schmiedl, G.2
Ball, W.A.3
Bund, J.4
Hellmann, G.5
Erdelmeier, I.6
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6
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0034639441
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(a) H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 58;
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Blackwell, H.E.1
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Bussmann, D.A.5
Grubbs, R.H.6
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7
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0034685462
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A. K. Chatterjee, J. P. Morgan, M. Scholl and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 3783.
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Chatterjee, A.K.1
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Scholl, M.3
Grubbs, R.H.4
-
8
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0016850334
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(-)-8-Phenylmenthyl acrylate required in the preparation of compound 10 was obtained by the method of E. J. Corey and H. E. Ensley, J. Am. Chem. Soc., 1975, 97, 6908.
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Corey, E.J.1
Ensley, H.E.2
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12
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0001373911
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ed. I. Ojima, VCH Publishers, New York
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(c) R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH Publishers, New York, 1993, pp. 103-158.
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Johnson, R.A.1
Sharpless, K.B.2
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13
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1642496074
-
-
note
-
9 but subsequently confirmed by chemical correlation studies (see text).
-
-
-
-
14
-
-
1642455057
-
-
note
-
This material was purchased from TCI, Japan.
-
-
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16
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0028216817
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(b) B. Mezrhab, F. Dumas, J. d'Angelo and C. Riche, J. Org. Chem., 1994, 59, 500.
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Mezrhab, B.1
Dumas, F.2
D'Angelo, J.3
Riche, C.4
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18
-
-
1642455058
-
-
note
-
t (major enantiomer): 12.2 min; (minor enantiomer): 14.8 min.
-
-
-
-
19
-
-
1642536823
-
-
note
-
t (major enantiomer): 12.3 min; (minor enantiomer): 14.9 min.
-
-
-
-
20
-
-
0000070865
-
-
(a) D. A. Evans, G. S. Peterson, J. S. Johnson, D. M. Barnes, K. R. Campos and K. A. Woerpel, J. Org. Chem., 1998, 63, 4541.
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Evans, D.A.1
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Campos, K.R.5
Woerpel, K.A.6
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21
-
-
0033936085
-
-
and references cited therein
-
For an excellent review of the applications of these complexes in synthesis see; (b) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325 and references cited therein.
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Johnson, J.S.1
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23
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0001594845
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(b) D. A. Evans, M. M. Morrissey and R. L. Dorow, J. Am. Chem. Soc., 1985, 107, 4346.
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Evans, D.A.1
Morrissey, M.M.2
Dorow, R.L.3
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24
-
-
1642455059
-
-
note
-
t (major enantiomer): 15.3 min; (minor enantiomer): 13.6 min.
-
-
-
-
26
-
-
22044458544
-
-
(b) D.-C. Ha, S.-H. Park, K.-S. Choi and C.-S. Yun, Bull. Korean Chem. Soc., 1998, 19, 728;
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Ha, D.-C.1
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0033617380
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(c) O. David, J. Blot, C. Bellec, M.-C. Fargeau-Bellassoued, G. Haviari, J.-P. Célérier, G. Lhommet, J.-C. Gramain and D. Gardette, J. Org. Chem., 1999, 64, 3122;
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David, O.1
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Haviari, G.5
Célérier, J.-P.6
Lhommet, G.7
Gramain, J.-C.8
Gardette, D.9
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28
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0032886125
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(d) S.-H, Kim, S.-I. Kim, S. Lai and J. K. Cha, J. Org. Chem., 1999, 64, 6771.
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30
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0036192333
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3 see: (b) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Tetrahedron Lett., 2001, 42, 8063; (c) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Synthesis, 2001, 2165.
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Babu, S.A.1
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31
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0035813428
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3 see: (b) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Tetrahedron Lett., 2001, 42, 8063; (c) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Synthesis, 2001, 2165.
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Yadav, J.S.1
Abraham, S.2
Reddy, B.V.S.3
Sabitha, G.4
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32
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0034752060
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3 see: (b) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Tetrahedron Lett., 2001, 42, 8063; (c) J. S. Yadav, S. Abraham, B. V. S. Reddy and G. Sabitha, Synthesis, 2001, 2165.
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Synthesis
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Yadav, J.S.1
Abraham, S.2
Reddy, B.V.S.3
Sabitha, G.4
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