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1
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0001753196
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M. Mulliez, Tetrahedron, 1981, 37, 2027-2041; also: N. E. Jacobsen and P. A. Bartlett, J. Am. Chem. Soc., 1983, 105, 1613-1619.
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(1981)
Tetrahedron
, vol.37
, pp. 2027-2041
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Mulliez, M.1
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2
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33845551995
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M. Mulliez, Tetrahedron, 1981, 37, 2027-2041; also: N. E. Jacobsen and P. A. Bartlett, J. Am. Chem. Soc., 1983, 105, 1613-1619.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 1613-1619
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Jacobsen, N.E.1
Bartlett, P.A.2
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4
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0042284352
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F. Dujols, P. Jollet and M. Mulliez, Phosphorus Sulfur Silicon Relat. Elem., 1998, 134-135, 231-254.
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(1998)
Phosphorus Sulfur Silicon Relat. Elem.
, vol.134-135
, pp. 231-254
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Dujols, F.1
Jollet, P.2
Mulliez, M.3
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9
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37049101835
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C. Brown, J. A. Boudreau, B. Hewitson and R. F. Hudson, J. Chem. Soc., Perkin Trans. 2, 1976, 888-895.
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(1976)
J. Chem. Soc., Perkin Trans.
, vol.2
, pp. 888-895
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Brown, C.1
Boudreau, J.A.2
Hewitson, B.3
Hudson, R.F.4
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10
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0000183594
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D. B. Cooper, C. R. Hall, J. M. Harrisson and T. D. Inch, J. Chem. Soc., Perkin Trans. 1, 1977, 1969-1980.
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(1977)
J. Chem. Soc., Perkin Trans.
, vol.1
, pp. 1969-1980
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Cooper, D.B.1
Hall, C.R.2
Harrisson, J.M.3
Inch, T.D.4
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11
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12844249276
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See particularly: R. J. Edmundson and T. A. Moran, J. Chem. Soc., 1971, 3437-3441. However with prior silylation a clean acylation occurs: M. Mulliez, Bull. Soc. Chim. Fr., 1985, 1211-1218.
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(1971)
J. Chem. Soc.
, pp. 3437-3441
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Edmundson, R.J.1
Moran, T.A.2
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12
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0006894834
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See particularly: R. J. Edmundson and T. A. Moran, J. Chem. Soc., 1971, 3437-3441. However with prior silylation a clean acylation occurs: M. Mulliez, Bull. Soc. Chim. Fr., 1985, 1211-1218.
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(1985)
Bull. Soc. Chim. Fr.
, pp. 1211-1218
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Mulliez, M.1
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13
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12844256248
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in preparation; F. Dujols' thesis (Université Paul Sabatier, Toulouse (France), 4-10-99), chapter VI
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P. Cazabonne, F. Dujols and M. Mulliez, Synthesis of constrained N-sulfonylated amino-alcohols, in preparation; F. Dujols' thesis (Université Paul Sabatier, Toulouse (France), 4-10-99), chapter VI.
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Synthesis of Constrained N-sulfonylated Amino-alcohols
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Cazabonne, P.1
Dujols, F.2
Mulliez, M.3
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17
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0016373003
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T. Koizumi, Y. Watanabe, Y. Yoshida and E. Yoshii, Tetrahedron Lett., 1974, 1075-1078.
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(1974)
Tetrahedron Lett.
, pp. 1075-1078
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Koizumi, T.1
Watanabe, Y.2
Yoshida, Y.3
Yoshii, E.4
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19
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12844252334
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note
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9 occurs with inversion of the phosphorus configuration. A priori the access to the requisite chiral heterocycles should be easy (simple separation of diastereoisomers), using chiral aminoacids instead of sarcosine (in 8c) and N phenylglycine (in 8d).
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20
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33646182572
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One should note that generally hydrolysis or alcoholysis are favoured over aminolysis: thermodynamically P-O bonds are stronger than PN bonds and usually amino P(v) intermediates are less stable. For a discussion of this problem see: J. M. Grévy and M. Mulliez, J. Chem. Soc., Perkin Trans. 2, 1995, 1809-1815.
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(1995)
J. Chem. Soc., Perkin Trans. 2
, pp. 1809-1815
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Grévy, J.M.1
Mulliez, M.2
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23
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0030818538
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R. Hirschmann, K. M. Yager, C. M. Taylor, J. Witherington, P. A. Sprengler, B. W. Phillips, W. Moore and A. B. Smith. J. Am. Chem. Soc., 1997, 119, 8177-8190.
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(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8177-8190
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Hirschmann, R.1
Yager, K.M.2
Taylor, C.M.3
Witherington, J.4
Sprengler, P.A.5
Phillips, B.W.6
Moore, W.7
Smith, A.B.8
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24
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3643137817
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This would allow the repetitive synthesis of sulfonopcptides: B. Garrigues and M. Mulliez, Phosphorus Sulfur Silicon Relat. Elem., 1991, 57, 203-209, if the insertion of the sulfonyl into the heterocycle does not bring about an exaltation of the reactivity of sulfur higher than that of phosphorus: T. Graafland, A. Wagenaar, A. J. Kirby and J. B. F. M. Engberts, J. Am. Chem. Soc., 1979, 101, 6981-6991.
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(1991)
Phosphorus Sulfur Silicon Relat. Elem.
, vol.57
, pp. 203-209
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Garrigues, B.1
Mulliez, M.2
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25
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0018784201
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This would allow the repetitive synthesis of sulfonopcptides: B. Garrigues and M. Mulliez, Phosphorus Sulfur Silicon Relat. Elem., 1991, 57, 203-209, if the insertion of the sulfonyl into the heterocycle does not bring about an exaltation of the reactivity of sulfur higher than that of phosphorus: T. Graafland, A. Wagenaar, A. J. Kirby and J. B. F. M. Engberts, J. Am. Chem. Soc., 1979, 101, 6981-6991.
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(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 6981-6991
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Graafland, T.1
Wagenaar, A.2
Kirby, A.J.3
Engberts, J.B.F.M.4
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27
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12844249893
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For more details refer to F. Dujols' thesis (Université Paul Sabatier, Toulouse (France), 4-10-99) and L. Marty's DEA des biomolecules (predoctoral study) report (02-91: independently of ref. 12)
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For more details refer to F. Dujols' thesis (Université Paul Sabatier, Toulouse (France), 4-10-99) and L. Marty's DEA des biomolecules (predoctoral study) report (02-91: independently of ref. 12).
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