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Volumn 5, Issue 11, 2010, Pages 2351-2354

A heterobimetallic Ni/La-salan complex for catalytic asymmetric decarboxylative 1,4-addition of malonic acid half-thioester

Author keywords

asymmetric catalysis; asymmetric synthesis; drug design; enantioselectivity; Schiff bases

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; DRUG DESIGN; ENANTIOSELECTIVE; HETEROBIMETALLICS; MALONIC ACID; NITROALKENES; SCHIFF BASIS; THIOESTERS;

EID: 78349300216     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000540     Document Type: Article
Times cited : (74)

References (73)
  • 6
    • 33846842435 scopus 로고    scopus 로고
    • For related works from other group, see
    • K. C. Fortner, M. D. Shair, J. Am. Chem. Soc. 2007, 129, 1032; For related works from other group, see
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 1032
    • Fortner, K.C.1    Shair, M.D.2
  • 9
    • 34548771245 scopus 로고    scopus 로고
    • For related works on decarboxylative 1,4-addition of β-keto acids to nitroalkenes, see
    • Angew. Chem. Int. Ed. 2007, 46, 6841; For related works on decarboxylative 1,4-addition of β-keto acids to nitroalkenes, see
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6841
  • 11
  • 13
    • 33846828385 scopus 로고    scopus 로고
    • A review on stereoselective synthesis of γ-amino acids
    • A review on stereoselective synthesis of γ-amino acids:, M. Ordóñez, C. Cativiela, Tetrahedron: Asymmetry 2007, 18, 3.
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 3
    • Ordóñez, M.1    Cativiela, C.2
  • 14
    • 0036089366 scopus 로고    scopus 로고
    • General reviews on asymmetric 1,4-addition to electron-deficient alkenes with metal catalysis
    • A review on asymmetric 1,4-addition to nitroalkenes O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877; General reviews on asymmetric 1,4-addition to electron-deficient alkenes with metal catalysis
    • (2002) Eur. J. Org. Chem. , pp. 1877
    • Berner, O.M.1    Tedeschi, L.2    Enders, D.3
  • 16
    • 34250613134 scopus 로고    scopus 로고
    • For selected leading examples of metal-catalyzed highly enantioselective 1,4-addition to nitroalkenes using nucleophiles other than MAHTs, such as 1,3-dicarbonyl compounds, under proton transfer conditions, see
    • S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701. For selected leading examples of metal-catalyzed highly enantioselective 1,4-addition to nitroalkenes using nucleophiles other than MAHTs, such as 1,3-dicarbonyl compounds, under proton transfer conditions, see
    • (2007) Eur. J. Org. Chem. , pp. 1701
    • Tsogoeva, S.B.1
  • 26
    • 77950515233 scopus 로고    scopus 로고
    • For a review on bimetallic Schiff base catalysts
    • For a review on bimetallic Schiff base catalysts:, R. M. Haak, S. J. Wezenberg, A. W. Kleij, Chem. Commun. 2010, 46, 2713.
    • (2010) Chem. Commun. , vol.46 , pp. 2713
    • Haak, R.M.1    Wezenberg, S.J.2    Kleij, A.W.3
  • 27
    • 34247463317 scopus 로고    scopus 로고
    • For heterobimetallic Schiff base catalysts containing rare earth metals, see
    • For heterobimetallic Schiff base catalysts containing rare earth metals, see, S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 4900
    • Handa, S.1    Gnanadesikan, V.2    Matsunaga, S.3    Shibasaki, M.4
  • 32
    • 0037424485 scopus 로고    scopus 로고
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see
    • For selected examples of related bifunctional bimetallic Schiff base complexes in asymmetric catalysis, see, V. Annamalai, E. F. DiMauro, P. J. Carroll, M. C. Kozlowski, J. Org. Chem. 2003, 68, 1973
    • (2003) J. Org. Chem. , vol.68 , pp. 1973
    • Annamalai, V.1    Dimauro, E.F.2    Carroll, P.J.3    Kozlowski, M.C.4
  • 41
    • 59049103335 scopus 로고    scopus 로고
    • For other examples, see review in Ref. [9]
    • Angew. Chem. Int. Ed. 2009, 48, 1126. For other examples, see review in Ref. [9].
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1126
  • 47
    • 77952572339 scopus 로고    scopus 로고
    • For selected recent reports using salan and salalen metal catalysts, see
    • For selected recent reports using salan and salalen metal catalysts, see, H. Egami, T. Oguma, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 5886
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5886
    • Egami, H.1    Oguma, T.2    Katsuki, T.3
  • 59
    • 0032192283 scopus 로고    scopus 로고
    • The utility of achiral phosphine oxides to modify the catalytic properties of rare earth metal catalysts, see, For recent selected examples, see also
    • The utility of achiral phosphine oxides to modify the catalytic properties of rare earth metal catalysts, see, K. Daikai, M. Kamaura, J. Inanaga, Tetrahedron Lett. 1998, 39, 7321; For recent selected examples, see also
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7321
    • Daikai, K.1    Kamaura, M.2    Inanaga, J.3
  • 62
    • 78349283645 scopus 로고    scopus 로고
    • Preliminary trials of diastereo- and enantioselective reactions using methyl substituted MAHT resulted in poor diastereo- and enantioselectivity. Further studies to overcome this limitation are ongoing
    • Preliminary trials of diastereo- and enantioselective reactions using methyl substituted MAHT resulted in poor diastereo- and enantioselectivity. Further studies to overcome this limitation are ongoing.
  • 63
    • 84987039439 scopus 로고
    • For catalytic asymmetric synthesis of rolipram by catalytic asymmetric 1,4-addition of malonates to nitroalkenes, see
    • A review on stereoselective synthesis of rolipram J. Mulzer, J. Prakt. Chem. 1994, 336, 287; For catalytic asymmetric synthesis of rolipram by catalytic asymmetric 1,4-addition of malonates to nitroalkenes, see
    • (1994) J. Prakt. Chem. , vol.336 , pp. 287
    • Mulzer, J.1
  • 65
    • 45849102419 scopus 로고    scopus 로고
    • For selected examples of other catalytic asymmetric approaches, see also
    • P. S. Hynes, P. A. Stupple, D. J. Dixon, Org. Lett. 2008, 10, 1389; For selected examples of other catalytic asymmetric approaches, see also
    • (2008) Org. Lett. , vol.10 , pp. 1389
    • Hynes, P.S.1    Stupple, P.A.2    Dixon, D.J.3
  • 71
    • 48749133072 scopus 로고    scopus 로고
    • See, also Ref. [4a]
    • Angew. Chem. Int. Ed. 2008, 47, 4719. See, also Ref. [4a].
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4719
  • 72
    • 60749108926 scopus 로고    scopus 로고
    • On the basis of our previous studies on Lewis base-assisted- Br×nsted base catalysis, we speculate that Lewis basic phosphine oxides would increase the Br×nsted basicity of La-aryloxide and/or increase the nucleophilicity of La-enolate species, see
    • On the basis of our previous studies on Lewis base-assisted- Br×nsted base catalysis, we speculate that Lewis basic phosphine oxides would increase the Br×nsted basicity of La-aryloxide and/or increase the nucleophilicity of La-enolate species, see:, H. Morimoto, T. Yoshino, T. Yukawa, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 9265
    • (2008) Angew. Chem. , vol.120 , pp. 9265
    • Morimoto, H.1    Yoshino, T.2    Yukawa, T.3    Lu, G.4    Matsunaga, S.5    Shibasaki, M.6


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