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Volumn 3, Issue 2, 2005, Pages 227-232

Phospholidines incorporating a β N-sulfonylaminoalcohol moiety: First observed selectivity of phosphorus heterocycle aminolysis in the presence of water

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); WATER;

EID: 12844261713     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415285a     Document Type: Article
Times cited : (4)

References (29)
  • 1
    • 0001753196 scopus 로고
    • M. Mulliez, Tetrahedron, 1981, 37, 2027-2041; also: N. E. Jacobsen and P. A. Bartlett, J. Am. Chem. Soc., 1983, 105, 1613-1619.
    • (1981) Tetrahedron , vol.37 , pp. 2027-2041
    • Mulliez, M.1
  • 11
    • 12844249276 scopus 로고
    • 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.
    • (1971) J. Chem. Soc. , pp. 3437-3441
    • Edmundson, R.J.1    Moran, T.A.2
  • 12
    • 0006894834 scopus 로고
    • 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.
    • (1985) Bull. Soc. Chim. Fr. , pp. 1211-1218
    • Mulliez, M.1
  • 19
    • 12844252334 scopus 로고    scopus 로고
    • note
    • 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).
  • 20
    • 33646182572 scopus 로고
    • 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.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1809-1815
    • Grévy, J.M.1    Mulliez, M.2
  • 24
    • 3643137817 scopus 로고
    • 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.
    • (1991) Phosphorus Sulfur Silicon Relat. Elem. , vol.57 , pp. 203-209
    • Garrigues, B.1    Mulliez, M.2
  • 25
    • 0018784201 scopus 로고
    • 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.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6981-6991
    • Graafland, T.1    Wagenaar, A.2    Kirby, A.J.3    Engberts, J.B.F.M.4
  • 27
    • 12844249893 scopus 로고    scopus 로고
    • 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)
    • 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).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.