Highly enantioselective [4+2] annulation via organocatalytic Mannich-reductive cyclization: one-pot synthesis of functionalized piperidines

A new method for one-pot synthesis of 2,3-substituted piperidine from N-PMP aldimine and aqueous glutaraldehyde via formal [4+2] cycloaddition is reported. This reaction involves organocatalytic direct Mannich reaction-reductive cyclization with high yields (up to 90%) and excellent enantioselectivi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2013-01, Vol.49 (50), p.5645-5647
Main Authors: Kumar, Indresh, Ramaraju, Panduga, Mir, Nisar A, Singh, Deepika, Gupta, Vivek K, Rajnikant
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cycloaddition Reaction
Glutaral - chemistry
Imines - chemistry
Piperidines - chemistry
Stereoisomerism
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Summary:A new method for one-pot synthesis of 2,3-substituted piperidine from N-PMP aldimine and aqueous glutaraldehyde via formal [4+2] cycloaddition is reported. This reaction involves organocatalytic direct Mannich reaction-reductive cyclization with high yields (up to 90%) and excellent enantioselectivities (up to >99%). The practicability of this method is also shown at a gram scale as well as through the synthesis of functionalized (-)-anabasine.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc42431f