π-Face selectivities in nucleophilic additions to 2-endo-arylnorbornan-7-ones: the role of through-space electrostatic interactions
Abstract
Experimental diastereoselectivities in hydride reduction of 2-endo-arylnorbornan-7-ones and computed transition state energetics reveal that the facial selectivity in these systems is predominantly determined by repulsions between the approaching nucleophile and the electron cloud of the aryl ring.