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Volumn 69, Issue 4, 2004, Pages 1038-1052

Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization/Bicyclization of Sterically Encumbered Substrates. Scope, Selectivity, and Catalyst Thermal Stability for Amine-Tethered Unactivated 1,2-Disubstituted Alkenes

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYST ACTIVITY; CATALYSTS; STEREOCHEMISTRY; THERMODYNAMIC STABILITY;

EID: 1242352508     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035417c     Document Type: Article
Times cited : (157)

References (154)
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    • (d) Ir-catalyzed asymmetric hydroamination of norbornene: Aufdenblatten, R.; Diezi, S.; Togni, A. Monatsh. Chem. 2000, 131, 1345-1350. Dorta, R.; Egli, P.; Zurcher, F.; Togni, A. J. Am. Chem. Soc. 1988, 119, 10857-10858.
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    • (d) Ir-catalyzed asymmetric hydroamination of norbornene: Aufdenblatten, R.; Diezi, S.; Togni, A. Monatsh. Chem. 2000, 131, 1345-1350. Dorta, R.; Egli, P.; Zurcher, F.; Togni, A. J. Am. Chem. Soc. 1988, 119, 10857-10858.
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    • Dorta, R.1    Egli, P.2    Zurcher, F.3    Togni, A.4
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    • note
    • Long reaction times (3-12 days) and low to moderate chemical yields (5-50%) are observed for Ir and Rh.
  • 21
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    • For recent reviews of catalytic amine addition to C-C multiple bonds, see: (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 104-114
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    • ref 1
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    • For hydroaminations mediated by early transition metals, see: (a) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 6, 935-946.
    • (2003) Eur. J. Org. Chem. , vol.6 , pp. 935-946
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    • Reference 3a,c
    • For hydroamination mediated by late transition metals, see: (a) Reference 3a,c.
  • 47
    • 1242268889 scopus 로고    scopus 로고
    • Reference 4
    • (b) Reference 4.
  • 48
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    • Reference 7
    • (c) Reference 7.
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    • For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850.
    • (2002) Chem. Rev. , vol.102 , pp. 1807-1850
    • Aspinall, H.C.1
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    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., Chapter 2
    • (h) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2.
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    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K.; Chapter 21
    • (l) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
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  • 118
    • 1242313908 scopus 로고    scopus 로고
    • note
    • A substrate bearing an α-methyl substituent such as 2-aminohept-5-ene (18) exhibits a relatively long induction period.
  • 123
    • 1242291474 scopus 로고    scopus 로고
    • note
    • 2LnR catalysts is highly dependent on Ln ion size.17b
  • 131
    • 1242313909 scopus 로고    scopus 로고
    • note
    • In this study, generally 5 mol % of chiral catalysts were employed in asymmetric hydroamination/cyclization. Thus, a 20-fold excess propylamine was employed to achieve consistent results.
  • 132
    • 1242291473 scopus 로고    scopus 로고
    • note
    • (a) Representative eight-coordinate effective ionic radii: La(III), 1. 160 Å; Nd(III), 1.109 Å; Sm(III), 1.079 Å; Y(III), 1.019 Å; Yb(III), 0.985 Å; Lu(III), 0.977 Å.
  • 136
    • 1242268892 scopus 로고    scopus 로고
    • note
    • Parameters in parentheses represent 3σ values derived from the least-squares fit.
  • 145
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    • note
    • 8 instantaneously turn to the characteristic blue and yellow colors, respectively, of the corresponding amine-amido complexes with initiation of catalytic turnover. Upon consumption of the amine substrates, the resulting reaction solutions return to the original colors.
  • 146
    • 1242291469 scopus 로고    scopus 로고
    • note
    • 6, and the results were identical.
  • 147
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    • note
    • For previous examples of organolanthanide-catalyzed tandem bicyclizations, see refs 22 and 23.
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    • note
    • Similar trends are observed in the cyclization of amine-tethered terminal olefin 22 → 23 mediated by CGCLn (e.g., Nd, 10:1; Sm, 10:1; Yb, 21:1).30
  • 151
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    • Reference 28
    • (b) Reference 28.
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    • Reference 29a
    • (c) Reference 29a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.