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Volumn 133, Issue 15, 2011, Pages 5791-5793

Catalytic asymmetric ring-opening of meso- aziridines with malonates under heterodinuclear rare earth metal Schiff base catalysis

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; ASYMMETRIC RINGS; AZIRIDINES; HETEROBIMETALLICS; MALONATES; RARE EARTH METALS; RING OPENING REACTION; SCHIFF-BASE; SEVEN-MEMBERED RINGS;

EID: 79954463686     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201492x     Document Type: Article
Times cited : (97)

References (37)
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    • For an alternative approach via asymmetric conjugate addition of malonates to 3-nitro-2 H -chromenes, see:;;; Tetrahedron Lett. 2010, 51, 3972
    • Guo, L.; Chi, Y.; Almeida, A. M.; Guzei, I. A.; Parker, B. K.; Gellman, S. H. J. Am. Chem. Soc. 2009, 131, 16018 For an alternative approach via asymmetric conjugate addition of malonates to 3-nitro-2 H -chromenes, see: Chen, W.-Y.; Ouyang, L.; Chen, R.-Y.; Li, X.-S. Tetrahedron Lett. 2010, 51, 3972
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16018
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    • Catalytic enantioselective alkylation of β-keto esters with unsubstituted aziridines has been reported, see
    • Catalytic enantioselective alkylation of β-keto esters with unsubstituted aziridines has been reported, see: Moss, T. A.; Fenwick, D. R.; Dixon, D. J. J. Am. Chem. Soc. 2008, 130, 10076
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10076
    • Moss, T.A.1    Fenwick, D.R.2    Dixon, D.J.3
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    • Aziridine ring-opening desymmetrization with azide
    • Aziridine ring-opening desymmetrization with azide: Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611
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    • Aziridine ring-opening with other nucleophiles, see Grignard reagent: Müller, P.; Nury, P. Org. Lett. 1999, 1, 439 Anilines: Arai, K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 8103 Thiols: Della Sala, G.; Lattanzi, A. Org. Lett. 2009, 11, 3330
    • (1999) Org. Lett. , vol.1 , pp. 439
    • Müller, P.1    Nury, P.2    Arai, K.3    Lucarini, S.4    Salter, M.M.5    Ohta, K.6    Yamashita, Y.7    Kobayashi, S.8    Della Sala, G.9    Lattanzi, A.10
  • 27
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    • For selected examples of bifunctional heterobimetallic Schiff base complexes in asymmetric catalysis, see:;;;, and references therein
    • For selected examples of bifunctional heterobimetallic Schiff base complexes in asymmetric catalysis, see: Annamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 1973 and references therein
    • (2003) J. Org. Chem. , vol.68 , pp. 1973
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    • Evaluation of the relative Lewis acidity of rare earth metals:;;, The reactivity changed in correlation with Lewis acidity of rare earth metal triflate (Yb, Y > Gd > Sm > La)
    • Evaluation of the relative Lewis acidity of rare earth metals: Tsuruta, H.; Yamaguchi, K.; Imamoto, T. Chem. Commun 1999, 1703 The reactivity changed in correlation with Lewis acidity of rare earth metal triflate (Yb, Y > Gd > Sm > La)
    • (1999) Chem. Commun , pp. 1703
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    • 3. For Lewis acid-promoted rearrangement of N -acylaziridines into oxazolines, see
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    • The addition of catalytic amount of amine base was effective to suppress the undesired Lewis acid-promoted intramolecular rearrangement of aziridines 2 to 2-aryloxazolines, and to promote the desired intermolecular reaction of malonate 3a with aziridines 2.
    • The addition of catalytic amount of amine base was effective to suppress the undesired Lewis acid-promoted intramolecular rearrangement of aziridines 2 to 2-aryloxazolines, and to promote the desired intermolecular reaction of malonate 3a with aziridines 2.
  • 37
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    • The reactions were run using 10 mol % catalyst loading in entries 7-13, because the reactivity of aziridines 2b - 2h was lower than that of aziridine 2a.
    • The reactions were run using 10 mol % catalyst loading in entries 7-13, because the reactivity of aziridines 2b - 2h was lower than that of aziridine 2a.


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