Asymmetric organocatalytic Michael addition/aza-cyclization coupled with sequential Michael addition for synthesizing densely polycyclic-fused dihydroquinolines

[Display omitted] A highly efficient sequential process based on organocatalysis for the asymmetric synthesis of polycyclic-fused dihydroquinolines is described. In this synthesis, an asymmetric organocatalytic Michael/aza-cyclization domino reaction of 5-formylpent-2-enyl esters with N-protected-2-...

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Bibliographic Details
Published in:Tetrahedron letters 2015-07, Vol.56 (28), p.4159-4162
Main Authors: Yu, Mirim, Kim, Sung-Gon
Format: Article
Language:English
Subjects:
1,4-Dihydroquinoline
Asymmetric catalysis
Aza-cyclization
Domino reaction
Organocatalysis
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Summary:[Display omitted] A highly efficient sequential process based on organocatalysis for the asymmetric synthesis of polycyclic-fused dihydroquinolines is described. In this synthesis, an asymmetric organocatalytic Michael/aza-cyclization domino reaction of 5-formylpent-2-enyl esters with N-protected-2-amino-β-nitrostyrenes, followed by dehydration, affords the corresponding α,β-unsaturated ester containing 1,4-dihydroquinoline products with high enantioselectivities (up to 99%ee). Subsequent organocatalytic intramolecular Michael reaction of the α,β-unsaturated ester containing 1,4-dihydroquinoline adducts results in the formation of chiral tricyclic-fused dihydroquinolines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.04.112