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Volumn 128, Issue 7, 2006, Pages 2286-2293

Stereochemistry of imine reduction by a hydroxycyclopentadienyl ruthenium hydride

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; COORDINATION REACTIONS; HYDROGEN; REDUCTION; STEREOCHEMISTRY;

EID: 33644552723     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056402u     Document Type: Article
Times cited : (61)

References (25)
  • 13
    • 0037007917 scopus 로고    scopus 로고
    • 1-S is an effective catalyst for the reduction of imines via hydrogen transfer from alcohols. Samec, J. S. M.; Bäckvall, J.-E. Chem. Eur. J. 2002, 8, 2955.
    • (2002) Chem. Eur. J. , vol.8 , pp. 2955
    • Samec, J.S.M.1    Bäckvall, J.-E.2
  • 18
    • 33644534614 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details of DFT calculations.
  • 19
    • 33644498965 scopus 로고    scopus 로고
    • note
    • Integrations were measured relative to the tolyl methyl group resonances, were within 5% of 1.00, and normalized to 1.00.
  • 23
    • 0000616566 scopus 로고
    • Nitrogen inversion is faster for arylamines than for alkylamines. The magnitude of the energy barrier to inversion in amines is correlated by the intergroup bond angle (α, C1-N-C2) and arylamines usually have larger intergroup bond angles (α, C1-N-C2) and are easier to invert. Both the wide angles and lower inversion barrier of arylamines are related to greater resonance stabilization by interaction with the arene π-system as planarity is approached. Koeppl, G. W.; Sagatys, D. S.; Krishnamurthy, G. S.; Miller, S. I. J. Am. Chem. Soc. 1967, 89, 3396.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3396
    • Koeppl, G.W.1    Sagatys, D.S.2    Krishnamurthy, G.S.3    Miller, S.I.4
  • 24
    • 33644552904 scopus 로고    scopus 로고
    • note
    • Another process that merits consideration is reversible dehydrogenation of intermediate B to give an anti-imine. This process, on its own, cannot account for loss of stereochemistry if only trans addition and elimination occur.
  • 25
    • 33644513854 scopus 로고    scopus 로고
    • note
    • If none of the aryl resonances were accidentally equivalent, then 28 peaks would be expected; 24 were seen.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.