Issue 21, 2013
From the journal:

RSC Advances

An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides†

Nayana Joseph,a   Rani Rajan,a   Jubi John,a   N. V. Devika,a   S. Sarath Chand,a   E. Suresh,b   Petri M. Pihko*c  and  K. V. Radhakrishnan*a  

* Corresponding authors

a Organic Chemistry Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695 019, India
E-mail: radhu2005@gmail.com

b Central Salt and Marine Chemicals Research Institute, Bhavnagar 364 002, India

c Department of Chemistry, University of Jyväskylä, Finland

Abstract

A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4-hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).

Graphical abstract: An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides

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Article information

DOI
https://doi.org/10.1039/C3RA41504J
Article type
Communication
Submitted
07 Mar 2013
Accepted
05 Apr 2013
First published
08 Apr 2013

RSC Adv., 2013,3, 7751-7757

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An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides

N. Joseph, R. Rajan, J. John, N. V. Devika, S. S. Chand, E. Suresh, P. M. Pihko and K. V. Radhakrishnan, RSC Adv., 2013, 3, 7751 DOI: 10.1039/C3RA41504J

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