Journal article

Pi-Facial Diastereoselectivity in the Electrophilic and Electrophilic Nucleophilic Additions to Dimethyl (1r,2r,3s,4s)-Bicyclo[2.2.2]Oct-5-Ene-2,3-Dicarboxylate

The pi-facial selectivity of attack of electrophilic species (OsO4, m-ClC6H4CO3H, BH3) on the sterically unbiased dimethyl (1R,2R,3S,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylate is controlled syn to the exo electron-withdrawing ester substituents, and the reactions of phenylselenyl chloride and phenylsulfenyl chloride show opposing diastereoselectivities, which can be explained using the Cieplak transition state theory.


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