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1 article(s) from Raftery, James

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

Pavol Jakubec,
Dane M. Cockfield,
Madeleine Helliwell,
James Raftery and
Darren J. Dixon

Beilstein J. Org. Chem. 2012, 8, 567–578, doi:10.3762/bjoc.8.64

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Graphical Abstract

Figure 1: Biologically active natural products and drugs containing the piperidine ring.

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Scheme 1: A general strategy to 5-nitropiperidin-2-ones and related heterocycles.

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Scheme 2: The synthesis of Michael adduct model substrates for the nitro-Mannich/lactamisation cascade.

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Scheme 3: Nitro-Mannich/lactamisation cascade with in situ formed imines.

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Figure 2: Cyclic imines employed in nitro-Mannich/lactamisation cascade.

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Scheme 4: Nitro-Mannich/lactamisation cascade of diastereomeric Michael adducts 6a, 6a’’ with cyclic imine 5a....

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Scheme 5: Nitro-Mannich/lactamisation cascade with cyclic imines. ^aDiastereomeric ratio in a crude reaction m...

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Scheme 6: Possible explanations for the observed high stereoselectivities in the nitro-Mannich/lactamisation ...

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Scheme 7: Thermodynamically-driven epimerisation of 5-nitropiperidin-2-ones 2m and 2m’.

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Figure 3: Thermodynamically driven epimerisation of 5-nitropiperidin-2-ones 2m and 2m’; identical diastereome...

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Scheme 8: One-pot three/four-component enantioselective Michael addition/nitro-Mannich/lactamisation cascade.

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Scheme 9: Protodenitration of 5-nitropiperidin-2-ones.

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Scheme 10: Various reductions of denitrated heterocycles.

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Published 16 Apr 2012

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