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Volumn 75, Issue 19, 2010, Pages 6588-6594

Axial-selective H/D exchange of glycine-derived 1 H -benzo[ e ][1,4]diazepin-2(3 H)-ones: Kinetic and computational studies of enantiomerization

Author keywords

[No Author keywords available]

Indexed keywords

COALESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 84961978359     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1010608     Document Type: Article
Times cited : (13)

References (33)
  • 8
    • 84962447226 scopus 로고    scopus 로고
    • Gawley R.E. Siegel J.S. Ed.; Topics in Stereochemistry;, Series Ed.; Verlag Helvetica Chimica Acta: Zürich
    • Carlier, P. R.; Hsu, D. C.; Bryson, S. A. In Stereochemical Aspects of Organolithium Compounds; Gawley, R. E., Ed.; Topics in Stereochemistry; Siegel, J. S., Series Ed.; Verlag Helvetica Chimica Acta: Zürich, 2010; Vol. 26, p 53 - 92.
    • (2010) Stereochemical Aspects of Organolithium Compounds , vol.26 , pp. 53-92
    • Carlier, P.R.1    Hsu, D.C.2    Bryson, S.A.3
  • 12
    • 84962382501 scopus 로고    scopus 로고
    • Note that we no longer favor the term "memory of chirality," in part because it is the configuration, not the "chirality" of the original stereogenic center that is "memorized." We believe that the term "self-regeneration of stereocenters via stereolabile axially chiral intermediates" is more accurate and descriptive. For additional justification 'f this term, see refs 8 and 9.
    • Note that we no longer favor the term "memory of chirality," in part because it is the configuration, not the "chirality" of the original stereogenic center that is "memorized." We believe that the term "self-regeneration of stereocenters via stereolabile axially chiral intermediates" is more accurate and descriptive. For additional justification of this term, see refs 8 and 9.
  • 13
    • 84962456776 scopus 로고    scopus 로고
    • The helical descriptors (M) and (P) are used to assign the sense of chirality of the ring, according to the sign of the C2N1C10C11 dihedral angle (M = minus, P = positive).
    • The helical descriptors (M) and (P) are used to assign the sense of chirality of the ring, according to the sign of the C2N1C10C11 dihedral angle (M = minus, P = positive).
  • 16
    • 84962382514 scopus 로고    scopus 로고
    • 1- 5d should be 6.5-fold less than the two-bond coupling constant of the axial and equatorial protons in 5d (10.5 Hz).
    • 1- 5d should be 6.5-fold less than the two-bond coupling constant of the axial and equatorial protons in 5d (10.5 Hz).
  • 17
    • 0004214389 scopus 로고
    • In; VCH Publishers: New York
    • Connors, K. A. In Chemical Kinetics; VCH Publishers: New York, 1990; pp 60 - 61.
    • (1990) Chemical Kinetics , pp. 60-61
    • Connors, K.A.1
  • 20
    • 84962371210 scopus 로고    scopus 로고
    • enant = 24.5 kcal/mol (298 K) and assumption of first-order racemization would predict <3% ee after 72 h.
    • enant = 24.5 kcal/mol (298 K) and assumption of first-order racemization would predict <3% ee after 72 h.
  • 22
    • 84962371208 scopus 로고    scopus 로고
    • enant(T) values, with and without PCM corrections.
    • enant(T) values, with and without PCM corrections.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.