6533b828fe1ef96bd1288ef7

RESEARCH PRODUCT

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

Kokkuvayil Vasu RadhakrishnanRani RajanNayana JosephN. V. DevikaJubi JohnShyam ChandPetri M. PihkoEringathodi Suresh

subject

Bicyclic moleculeChemistryGeneral Chemical EngineeringArylchemistry.chemical_elementHalideGeneral ChemistryRing (chemistry)Medicinal chemistryCatalysischemistry.chemical_compoundReagentOrganic chemistryStereoselectivityta116Palladium

description

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).

10.1039/c3ra41504jhttp://juuli.fi/Record/0036868913