Issue 55, 2012
From the journal:

Chemical Communications

An organocatalytic direct Mannich–cyclization cascade as [3+2] annulation: asymmetric synthesis of 2,3-substituted pyrrolidines†

Indresh Kumar,*ab   Nisar A. Mir,b   Vivek K. Guptac  and  Rajnikantc  

* Corresponding authors

a Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, Rajasthan, India
E-mail: indresh.chemistry@gmail.com, indresh.kumar@bits-pilani.ac.in
Fax: +91 1596 244183
Tel: +91 1596 245073 Ext 276

b School of Biology & Chemistry, College of Science, Shri Mata Vaishno Devi University, Katra 182 320, India

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

Abstract

A new method for asymmetric synthesis of 2,3-substituted pyrrolidines from N-PMP aldimines and succinaldehyde via formal [3+2] cycloaddition is reported. This reaction involves proline catalyzed direct Mannich reaction and acid catalyzed reductive cyclization with high yields (up to 78%) and excellent enantioselectivities (up to >99%).

Graphical abstract: An organocatalytic direct Mannich–cyclization cascade as [3+2] annulation: asymmetric synthesis of 2,3-substituted pyrrolidines

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Article information

DOI
https://doi.org/10.1039/C2CC33103A
Article type
Communication
Submitted
30 Apr 2012
Accepted
23 May 2012
First published
23 May 2012

Chem. Commun., 2012,48, 6975-6977

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An organocatalytic direct Mannich–cyclization cascade as [3+2] annulation: asymmetric synthesis of 2,3-substituted pyrrolidines

I. Kumar, N. A. Mir, V. K. Gupta and Rajnikant, Chem. Commun., 2012, 48, 6975 DOI: 10.1039/C2CC33103A

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