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Volumn 55, Issue 10, 1999, Pages 3025-3040

Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM METHYL 4 TOLYLSULFOXIDE; SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0033525459     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00064-2     Document Type: Article
Times cited : (49)

References (71)
  • 1
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    • Morrison, J. D., Ed.
    • For reviews see: (a) Solladiè, G. In Asymmetric Synthesis; Morrison, J. D., Ed.; 1983, Vol. 2.
    • (1983) Asymmetric Synthesis , vol.2
    • Solladiè, G.1
  • 3
    • 0004139460 scopus 로고
    • Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: New York
    • (c) Posner, G. H. In The Chemistry of Sulphones and Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: New York, 1988.
    • (1988) The Chemistry of Sulphones and Sulphoxides
    • Posner, G.H.1
  • 12
  • 14
  • 25
    • 0001784546 scopus 로고
    • For the addition of sulfoxide stabilized nucleophiles to the C=N bond of nitrones see: (i) Annunziata R.; Cinquini, M.; Cozzi, F. Synthesis 1982, 929-931.
    • (1982) Synthesis , pp. 929-931
    • Annunziata, R.1    Cinquini, M.2    Cozzi, F.3
  • 30
    • 0013566391 scopus 로고    scopus 로고
    • Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., Chapter 2
    • (a) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, D. C., 1996; Chapter 2.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
    • Soloshonok, V.A.1
  • 39
    • 0029971190 scopus 로고    scopus 로고
    • (d) Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S.V.; Zanda, M.; Crucianelli, M.; Cavicchio, G. J. Org. Chem. 1996, 61, 3375-3387; corrigenda: J. Org. Chem. 1996, 61, 9635.
    • (1996) J. Org. Chem. , vol.61 , pp. 9635
  • 45
    • 0003463148 scopus 로고
    • Wiley: London
    • PMP-Group is well-known as a versatile protecting group, and in most cases, can be subsequently removed to afford a free amino function; Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: London, 1991.
    • (1991) Protective Groups in Organic Synthesis
    • Greene, T.W.1    Wuts, P.G.M.2
  • 49
    • 0003462939 scopus 로고
    • Report ORNL-5138. Oak Ridge National Laboratory, Tennessee
    • (a) Johnson, C.K. 1976, ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee.
    • (1976) ORTEPII
    • Johnson, C.K.1
  • 50
    • 0013619545 scopus 로고    scopus 로고
    • Interesting feature in this structure is the gauche arrangement of the torsion angle S-C(1)-C(2)-N in the main chain that allows the p-fluoro-phenyl ring to lay in a plane almost orthogonal to the plane of the other two phenyl rings. The p-tolyl and the p-methoxy-phenyl rings are not coplanar for 7.3°. All bond distances and angles fall in the expected range. Weak interactions via quite long H-bonds are present between F, O(1), O(2) and hydrogen atoms of the nearest neighboring molecules
    • (b) Interesting feature in this structure is the gauche arrangement of the torsion angle S-C(1)-C(2)-N in the main chain that allows the p-fluoro-phenyl ring to lay in a plane almost orthogonal to the plane of the other two phenyl rings. The p-tolyl and the p-methoxy-phenyl rings are not coplanar for 7.3°. All bond distances and angles fall in the expected range. Weak interactions via quite long H-bonds are present between F, O(1), O(2) and hydrogen atoms of the nearest neighboring molecules.
  • 51
    • 0013590296 scopus 로고    scopus 로고
    • Atomic coordinates for the structure have been deposited with the Cambridge Crystallographic Data Centre and can be obtained on request from: The Director, Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, U.K.
    • (c) Atomic coordinates for the structure have been deposited with the Cambridge Crystallographic Data Centre and can be obtained on request from: The Director, Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, U.K.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.