Enantioselective Synthesis of N‑PMP-1,2-dihydropyridines via Formal [4 + 2] Cycloaddition between Aqueous Glutaraldehyde and Imines

A simple and highly practical one-pot formal [4 + 2] cycloaddition approach for the enantioselective synthesis of N-PMP-1,2-dihydropyridines (DHPs) is described. This chemistry involves an amino-catalytic direct Mannich reaction/cyclization followed by IBX-mediated chemo- and regioselective oxidatio...

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Bibliographic Details
Published in:Organic letters 2015-11, Vol.17 (22), p.5582-5585
Main Authors: Ramaraju, Panduga, Mir, Nisar A, Singh, Deepika, Gupta, Vivek K, Kant, Rajni, Kumar, Indresh
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cycloaddition Reaction
Dihydropyridines - chemistry
Glutaral - chemistry
Imines - chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:A simple and highly practical one-pot formal [4 + 2] cycloaddition approach for the enantioselective synthesis of N-PMP-1,2-dihydropyridines (DHPs) is described. This chemistry involves an amino-catalytic direct Mannich reaction/cyclization followed by IBX-mediated chemo- and regioselective oxidation sequence between readily available aqueous glutaraldehyde and imines under very mild conditions. A series of N-PMP-1,2-DHPs have been prepared in high yields and excellent enantioselectivity. This method also gives access to both enantiomers of 1,2-DHPs in surplus amount by shifting the catalyst configuration.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02744