메뉴 건너뛰기




Volumn 18, Issue 25, 2012, Pages 7654-7657

Mg-catalyzed enantioselective benzylic C-H bond functionalization of isoindolinones: Addition to imines

Author keywords

Asymmetric catalysis; C H activation; Imines; Isoindolinones; Magnesium

Indexed keywords

ALKENYL; ASYMMETRIC CATALYSIS; BASE CATALYST; BENZYLIC; C-H ACTIVATION; C-H BOND; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; FUNCTIONALIZATIONS; IMINES; ISOINDOLINONES;

EID: 84862593617     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200821     Document Type: Article
Times cited : (18)

References (57)
  • 24
    • 0037128491 scopus 로고    scopus 로고
    • for racemic reactions of isoindolinones with aldehydes via benzylic carbanion formation with stoichiometric amounts of LDA (LDA=lithium diisopropylamide), see: 1) A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau, V. Rys, Tetrahedron Lett. 2002, 43, 2207.
    • (2002) Rys, Tetrahedron Lett , vol.43 , pp. 2207
    • Couture, A.1    Deniau, E.2    Grandclaudon, P.3    Hoarau, V.C.4
  • 25
    • 77954271846 scopus 로고    scopus 로고
    • For a general review on enantioselective synthesis of tetrasubstituted oxindoles, see: a) F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381
    • (2010) Adv. Synth. Catal , vol.352 , pp. 1381
    • Zhou, F.1    Liu, Y.-L.2    Zhou, J.3
  • 26
    • 83755168278 scopus 로고    scopus 로고
    • for selected leading examples using oxindoles for asymmetric C-C bond formation, see: 1) B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc. 2011, 133, 20611, and references therein
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 20611
    • Trost, B.M.1    Xie, J.2    Sieber, J.D.3
  • 45
    • 84862614644 scopus 로고    scopus 로고
    • 2-pyridinesulfonyl imine, diphenylphosphinoyl imine, and Boc-imine resulted in much less satisfactory yield and/or enantioselectivity when using Bu2Mg/Schiff base catalysts
    • Other imines, such as Ts-imine (Ts=p-toluenesulfonyl), 2-pyridinesulfonyl imine, diphenylphosphinoyl imine, and Boc-imine resulted in much less satisfactory yield and/or enantioselectivity when using Bu2Mg/Schiff base catalysts.
    • Other Imines, Such As Ts-imine (Ts=p-toluenesulfonyl)
  • 46
    • 84862614267 scopus 로고    scopus 로고
    • For the utility of MeO-substituted Schiff base 2a and related ligands in asymmetric catalysis, see: A) B
    • For the utility of MeO-substituted Schiff base 2a and related ligands in asymmetric catalysis, see: a) B. Wu, J. C. Gallucci, J. R. Parquette, T. V. RajanBabu, Angew. Chem. 2009, 121, 1146
    • (2009) Wu, J , Issue.121 , pp. 1146
    • Gallucci, C.1    Parquette, J.R.2    RajanBabu, T.V.3
  • 47
  • 54
    • 84862608762 scopus 로고    scopus 로고
    • such as BINOL derivatives (BINOL=1,1-bi-2- naphtho1) and chiral bis-sulfonamides, resulted in poor reactivity and/or stereoselectivity
    • Other chiral ligands, such as BINOL derivatives (BINOL=1,1-bi-2- naphtho1) and chiral bis-sulfonamides, resulted in poor reactivity and/or stereoselectivity.
    • Other Chiral Ligands
  • 56
    • 84862608763 scopus 로고    scopus 로고
    • CCDC-870068 (syn-5a1) and CCDC-870069 (anti-5a1) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-870068 (syn-5a1) and CCDC-870069 (anti-5a1) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 57
    • 84862614565 scopus 로고    scopus 로고
    • Because the structure of the catalyst, prepared from Bu2Mg/Schiff base 2 (Figure 2) in a ratio of 1:1, has not been clarified, it is difficult to propose the transition state model to explain the stereochemistry of products
    • Because the structure of the catalyst, prepared from Bu2Mg/Schiff base 2 (Figure 2) in a ratio of 1:1, has not been clarified, it is difficult to propose the transition state model to explain the stereochemistry of products. The Bu2Mg/Schiff base 2 1:1 mixture is speculated to have an oligomeric structure, see ref. [14b].
    • The Bu2Mg/Schiff Base rfvn1 2 1:1 Mixture Is Speculated to Have An Oligomeric Structure, See Ref. [14b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.