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■ 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

Abstract

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.