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Volumn 46, Issue 31, 2005, Pages 5181-5185

A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

Author keywords

Chiral azomethine ylides; Pyrrolidine synthesis; Stereocontrolled 3+2 cycloadditions

Indexed keywords

AZOMETHINE YLIDE; IMINE; PYRROLIDINE DERIVATIVE;

EID: 21344472768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.119     Document Type: Article
Times cited : (26)

References (25)
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  • 4
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    • D.P. Curran JAI Press Greenwich CT
    • Reviews of azomethine ylide cycloaddition chemistry: R. Grigg, and V. Sridharan D.P. Curran Advances in Cycloaddition Vol. 3 1993 JAI Press Greenwich CT 161 204
    • (1993) Advances in Cycloaddition , vol.3 , pp. 161-204
    • Grigg, R.1    Sridharan, V.2
  • 15
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    • Additions to analogous nitrones suggested that the anti-selectivity should have been obtained with this substrate. See: P. Merino, S. Franco, F.L. Merchan, and T. Tejero J. Org. Chem. 63 1998 5627
    • (1998) J. Org. Chem. , vol.63 , pp. 5627
    • Merino, P.1    Franco, S.2    Merchan, F.L.3    Tejero, T.4
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    • P. Garner, and J.M. Park Org. Synth. 70 1991 18 The d-serinal derivative was actually used for these experiments. However, since we were only concerned with diastereoselectivity in these model studies, the reaction is depicted as if the l-antipode were used to facilitate stereochemical comparisons with the natural product
    • (1991) Org. Synth. , vol.70 , pp. 18
    • Garner, P.1    Park, J.M.2
  • 20
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    • Calculated LUMO energies for methyl acrylate and acrylamide are -1.900 eV and -1.403 eV, respectively. See: C.-G. Zhan, J.A. Nichols, and D.A. Dixon J. Phys. Chem. A 107 2003 4184
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.