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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1553-1563
Published online, 24th September, 2013
DOI: 10.3987/COM-13-S(S)85
Yb(OTf)3-Mediated Ring Opening of Functionalized Cyclopentane Epoxides with Aniline: Aspects of Regiochemistry and Stereochemistry

Stephen Hanessian* and Changwei Mu

*Department of Chemistry, University of Montreal, C.P. 6128, Succ. Centre-ville, Montréal, Québec H3C 3J7, Canada


The ring-opening reaction of cyclopentan-1-ol 2,3-epoxides bearing alkoxy and hydroxyl groups with aniline was studied in the presence of Yb(OTf)3 in refluxing toluene. The syn- and anti- relationship of the alkoxy group has an influence on the regioselectivity of attack affording aniline adducts at the secondary or tertiary position.