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Volumn 130, Issue 14, 2008, Pages 4669-4679

Direct measurement of the rate of interconversion of zirconaaziridine enantiomers

Author keywords

[No Author keywords available]

Indexed keywords

DYNAMIC KINETIC RESOLUTION (DKR); ENANTIOMER INTERCONVERSION;

EID: 41849126809     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0757935     Document Type: Article
Times cited : (18)

References (72)
  • 3
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    • Cummings, S. A.; Tunge, J. A.; Norton, J. R. Top. Organomet. Chem. 2005, 10, 1-39. Some of the results in the present manuscript were mentioned in this review as unpublished results without experimental details.
    • Cummings, S. A.; Tunge, J. A.; Norton, J. R. Top. Organomet. Chem. 2005, 10, 1-39. Some of the results in the present manuscript were mentioned in this review as "unpublished results" without experimental details.
  • 18
    • 0035801528 scopus 로고    scopus 로고
    • d,e (a) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. - Eur. J. 2001, 7, 3768-3775.
    • d,e (a) Trost, B. M.; Patterson, D. E.; Hembre, E. J. Chem. - Eur. J. 2001, 7, 3768-3775.
  • 19
    • 41849105936 scopus 로고    scopus 로고
    • The conversion with an enantiopure reagent of freely interconverting enantiomers of a chiral substrate into unequal amounts of two diastereomers can also be termed, simply, an asymmetric transformation. McNaught, A. D, Wilkinson, A. IUPAC Compendium of Chemical Terminology, 2nd ed, Royal Society of Chemistry: Cambridge, U.K, 1997
    • (b) The conversion with an enantiopure reagent of freely interconverting enantiomers of a chiral substrate into unequal amounts of two diastereomers can also be termed, simply, an "asymmetric transformation". McNaught, A. D.; Wilkinson, A. IUPAC Compendium of Chemical Terminology, 2nd ed.; Royal Society of Chemistry: Cambridge, U.K., 1997.
  • 20
    • 0003978131 scopus 로고
    • A kinetic resolution starts with a racemic mixture. See, Prentice Hall; Englewood Cliffs, NJ
    • (c) A kinetic resolution starts with a racemic mixture. See Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; Prentice Hall; Englewood Cliffs, NJ, 1971; pp 30-35.
    • (1971) Asymmetric Organic Reactions , pp. 30-35
    • Morrison, J.D.1    Mosher, H.S.2
  • 23
  • 34
    • 41849105215 scopus 로고    scopus 로고
    • The η3-azaallyl zirconium hydrides undergo insertion reactions via the isomeric zirconaaziridines, as can be inferred from refs 1 and 9
    • 3-azaallyl zirconium hydrides undergo insertion reactions via the isomeric zirconaaziridines, as can be inferred from refs 1 and 9.
  • 48
    • 41849086447 scopus 로고    scopus 로고
    • 2 imine about the axis linking it to the Zr. We think such imine rotation unlikely with an early transition metal, where the complex is better described as a metallaaziridine.
    • 2 imine about the axis linking it to the Zr. We think such "imine rotation" unlikely with an early transition metal, where the complex is better described as a metallaaziridine.
  • 49
    • 41849143955 scopus 로고    scopus 로고
    • 1 isomerization (Paul C under Mechanism), accelerated by the steric demands of the Me and Ph substituents, affects enantiomer interconversion even for 7.
    • 1 isomerization (Paul C under Mechanism), accelerated by the steric demands of the Me and Ph substituents, affects enantiomer interconversion even for 7.
  • 53
    • 41849145032 scopus 로고    scopus 로고
    • At the beginning of such a reaction, with the enantiomers of 10 present in equal amounts, the product ratio (R,R,R, R,R,S) will equal kR/kS
    • S.
  • 54
    • 41849101219 scopus 로고    scopus 로고
    • Ianni, J. Kintecus V3.8.
    • Ianni, J. Kintecus V3.8.
  • 55
    • 41849109294 scopus 로고    scopus 로고
    • S values for 2c (obtained by kinetic simulation) are reported as the standard deviation of each rate constant for two data sets.
    • S values for 2c (obtained by kinetic simulation) are reported as the standard deviation of each rate constant for two data sets.
  • 56
    • 41849083591 scopus 로고    scopus 로고
    • We know, from ref 1, that kinetic resolution leaves zirconaaziridine enriched in the R enantiomer for 1a and 1d and assumes that the configuration is the same in the other cases.
    • We know, from ref 1, that kinetic resolution leaves zirconaaziridine enriched in the R enantiomer for 1a and 1d and assumes that the configuration is the same in the other cases.
  • 57
    • 0004182966 scopus 로고
    • 2nd ed, Surfside: Gainesville, FL
    • Drago, R. Physical Methods for Chemists, 2nd ed.; Surfside: Gainesville, FL, 1992; pp 137-141.
    • (1992) Physical Methods for Chemists , pp. 137-141
    • Drago, R.1
  • 65
    • 0033537024 scopus 로고    scopus 로고
    • 2 equilibria in the reference they cite (their ref 18).
    • 2 equilibria in the reference they cite (their ref 18).
  • 69


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.