Issue 50, 2013
From the journal:

Chemical Communications

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

Indresh Kumar,*a   Panduga Ramaraju,a   Nisar A. Mir,a   Deepika Singh,b   Vivek K. Guptac  and  Rajnikantc  

* Corresponding authors

a Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India
E-mail: indresh.chemistry@gmail.com, indresh.kumar@pilani.bits-pilani.ac.in
Fax: +91 1596 244183
Tel: +91 1596 515707

b Instrumentation Division, IIIM-CSIR Lab, Jammu 180 001, India

c X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu 180 006, India

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC42431F
Article type
Communication
Submitted
05 Apr 2013
Accepted
03 May 2013
First published
03 May 2013

Chem. Commun., 2013,49, 5645-5647

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

I. Kumar, P. Ramaraju, N. A. Mir, D. Singh, V. K. Gupta and Rajnikant, Chem. Commun., 2013, 49, 5645 DOI: 10.1039/C3CC42431F

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