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Volumn 50, Issue 21, 2011, Pages 4928-4932

Highly enantioselective Michael addition of pyrazolin-5-ones catalyzed by chiral metal/N,N′-dioxide complexes: Metal-directed switch in enantioselectivity

Author keywords

asymmetric synthesis; homogeneous catalysis; Michael addition; nitrogen heterocycles; rare earth metals

Indexed keywords

ASYMMETRIC SYNTHESIS; HOMOGENEOUS CATALYSIS; MICHAEL ADDITION; NITROGEN HETEROCYCLES; RARE-EARTH METALS;

EID: 79955767991     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201008256     Document Type: Article
Times cited : (140)

References (90)
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    • For reviews of catalytic enantioselective construction of quaternary chiral centers, see
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    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1688
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    • For selected examples with 1,4-dicarbonyl but-2-enes as Michael acceptors, see
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    • CCDC798756 (3 k) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC798756 (3 k) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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    • 5OH: 90 % yield, 82:18d.r., 86 and 90 %ee for the respective diastereomers; iPrOH: 80 % yield, 80:20d.r., 67 and 77 %ee for the respective diastereomers; tBuOH: 60 % yield, 75:25d.r., 60 and 73 %ee for the respective diastereomers (see the Supporting Information).
    • 5OH: 90 % yield, 82:18d.r., 86 and 90 %ee for the respective diastereomers; iPrOH: 80 % yield, 80:20d.r., 67 and 77 %ee for the respective diastereomers; tBuOH: 60 % yield, 75:25d.r., 60 and 73 %ee for the respective diastereomers (see the Supporting Information).
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    • for a related concept in lanthanide metals with oxazoline-type ligands, see reference[3g].
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    • Kobayashi, S.1    Sugiura, M.2    Kitagawa, H.3    Lam, W.W.-L.4
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    • + was the main intermediate in the reaction, thus suggesting the possibility that a 4-substititued-5-pyrazolone serves as a ligand as well as a substrate (see the Supporting Information).
    • + was the main intermediate in the reaction, thus suggesting the possibility that a 4-substititued-5-pyrazolone serves as a ligand as well as a substrate (see the Supporting Information).


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