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Volumn 79, Issue 4, 2014, Pages 1796-1804

Regio- and stereoselective aminopentadienylation of carbonyl compounds

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EID: 84894533647     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402854z     Document Type: Article
Times cited : (12)

References (33)
  • 26
    • 66449094686 scopus 로고    scopus 로고
    • 1H NMR spectra, we have prepared authentic samples of diastereomeric mixtures for compounds 4a, e, f, h - j (see the Supporting Information) according to a reported procedure
    • 1H NMR spectra, we have prepared authentic samples of diastereomeric mixtures for compounds 4a, e, f, h-j (see the Supporting Information) according to a reported procedure: Brak, K.; Barrett, K. T.; Ellman, J. A. J. Org. Chem. 2009, 74, 3606
    • (2009) J. Org. Chem. , vol.74 , pp. 3606
    • Brak, K.1    Barrett, K.T.2    Ellman, J.A.3
  • 28
    • 0033575410 scopus 로고    scopus 로고
    • The Lewis acid catalyzed E / Z isomerization of tert -butylsulfinyl ketimines has already been reported. See
    • The Lewis acid catalyzed E / Z isomerization of tert -butylsulfinyl ketimines has already been reported. See: Cogan, D. A.; Liu, G.-C.; Ellman, J. Tetrahedron 1999, 55, 8883
    • (1999) Tetrahedron , vol.55 , pp. 8883
    • Cogan, D.A.1    Liu, G.-C.2    Ellman, J.3
  • 29
    • 0037250762 scopus 로고    scopus 로고
    • In these hypothetical transition states we did not define the geometry of the internal double bond of the pentadienyl moiety because it is not relevant to the stereochemical outcome of the reaction. In the case of aldimines it seems more reasonable to place the vinylic group in an equatorial position; however, gauche interactions along C2-C3 are more severe with ketimines. In fact, during the addition of pentadienyl indium reagents to α β-unsaturated ketones a transition state was proposed where the vinylic group occupies an axial position; see
    • In these hypothetical transition states we did not define the geometry of the internal double bond of the pentadienyl moiety because it is not relevant to the stereochemical outcome of the reaction. In the case of aldimines it seems more reasonable to place the vinylic group in an equatorial position; however, gauche interactions along C2-C3 are more severe with ketimines. In fact, during the addition of pentadienyl indium reagents to α,β-unsaturated ketones a transition state was proposed where the vinylic group occupies an axial position; see: Villalva-Servín, N. P.; Melekov, A.; Fallis, A. G. Synthesis 2003, 5, 790
    • (2003) Synthesis , vol.5 , pp. 790
    • Villalva-Servín, N.P.1    Melekov, A.2    Fallis, A.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.