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Paper | Special issue | Vol 84, No. 2, 2012, pp.843-878
Published online, 18th August, 2011
DOI: 10.3987/COM-11-S(P)65
Development of an Intramolecular Gassman’s [2+2] Cycloaddition

John B. Feltenberger, Changhong Ko, Jun Deng, Sunil K. Ghosh, and Richard P. Hsung*

*Department of Chemistry, Division of Pharmaceutical Sciences, University of Wisconsin, 777 Highland Aenue, Madison, WI 53705-2222, U.S.A.

Abstract

The development of an intramolecular variant of Gassman’s cationic [2 + 2] cycloaddition is described herein. Mechanistic aspects of the stepwise nature of this cycloaddition process between vinyl acetals and unactivated olefins have been studied. We have also explored the scope of this reaction with regard to various oxygen-, nitrogen-, and carbon-tethered acetals to provide access to a diverse array of bicyclic scaffolds. Additionally, we have identified vinyl hemiaminals as having favorable reactivity for cationic [2 + 2] cycloaddition.