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Volumn 5, Issue 9, 2010, Pages 2106-2112

Using a combination of magnetic anisotropic effects for the configurational assignment of amino alcohols

Author keywords

Absolute configuration; Amino alcohols; Chirality; Magnetic anisotropic effects; NMR spectroscopy

Indexed keywords

1 ,2-AMINO ALCOHOLS; ABSOLUTE CONFIGURATION; AMINO ALCOHOLS; ANISOTROPIC EFFECTS; HYDROGEN ATOMS; ISOTOPIC LABELING; LOW TEMPERATURES; METHOXY; NMR SPECTROSCOPY; REPRESENTATIVE COMPOUND; STEREOGENIC CARBON ATOMS;

EID: 77956462046     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000229     Document Type: Article
Times cited : (8)

References (42)
  • 10
    • 0000523834 scopus 로고    scopus 로고
    • (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York
    • f) G. Uray in Houben-Weyl Methods in Organic Chemistry, Vol 1 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, New York, 1996, p. 253
    • (1996) Houben-weyl Methods in Organic Chemistry , vol.1 , pp. 253
    • Uray In, G.1
  • 32
    • 77956468501 scopus 로고    scopus 로고
    • Secondary/primary and primary/secondary (sec/prim and prim/sec) apply only to the carbon atoms to which the amino/hydroxy groups are linked. Sphingosines and epinephrines (adrenalines) are examples of compounds of biological interest that bear these substructures.
    • Secondary/primary and primary/secondary (sec/prim and prim/sec) apply only to the carbon atoms to which the amino/hydroxy groups are linked. Sphingosines and epinephrines (adrenalines) are examples of compounds of biological interest that bear these substructures.
  • 33
    • 77956478776 scopus 로고    scopus 로고
    • Two approaches that do not make any use of δσRS from the substrate and are based on the cross-interaction between auxiliaries-just δσRS from the methoxy and methine groups of the MPAs-have been published recently. The method now described in this article is appropriate in cases in which the application of those previous approaches presents difficulties-that is, presence of extra methoxy groups in the substrate or overlapped methine signals-and is useful to double-check the configurational assignment.
    • Two approaches that do not make any use of δσRS from the substrate and are based on the cross-interaction between auxiliaries-just δσRS from the methoxy and methine groups of the MPAs-have been published recently. The method now described in this article is appropriate in cases in which the application of those previous approaches presents difficulties-that is, presence of extra methoxy groups in the substrate or overlapped methine signals-and is useful to double-check the configurational assignment.
  • 36
    • 77956483761 scopus 로고    scopus 로고
    • This approach avoids the use of protecting groups for the terminal primary group, thus making the experimental procedure much simpler.
    • This approach avoids the use of protecting groups for the terminal primary group, thus making the experimental procedure much simpler.
  • 37
    • 77956470279 scopus 로고    scopus 로고
    • See the Supporting Information for a full explanation of the confor-mational equilibria that justifies the δσRS signs in prim/sec benzylic amino alcohols.
    • See the Supporting Information for a full explanation of the confor-mational equilibria that justifies the δσRS signs in prim/sec benzylic amino alcohols.
  • 38
    • 77956465611 scopus 로고    scopus 로고
    • The gt conformer is defined as the one in which the benzoate is gauche to the benzamide and trans to the Me (sec/prim), or the ben-zamide is gauche to the benzoate and trans to the Me (prim/sec).
    • The gt conformer is defined as the one in which the benzoate is gauche to the benzamide and trans to the Me (sec/prim), or the ben-zamide is gauche to the benzoate and trans to the Me (prim/sec).
  • 42
    • 77956456872 scopus 로고    scopus 로고
    • 2' bond.
    • In this case, the lowest-energy conformer arises from a I conformation for the C1-N bond combined with a gg conformer for the C1'-C2' bond.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.