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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

Author:
Joseph, Nayana, Rajan, Rani, John, Jubi, Devika, N. V., Chand, S. Sarath, Suresh, E., Pihko, Petri M., Radhakrishnan, K. V.
Source:
RSC advances 2013 v.3 no.21 pp. 7751-7757
ISSN:
2046-2069
Subject:
alkenes, amines, antidepressants, catalytic activity, hydrazines, organic halogen compounds, palladium, stereoselectivity
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).
Agid:
6645155