G. Mehta et al., PI-FACE SELECTIVITIES IN NUCLEOPHILIC ADDITIONS TO 2-ENDO-ARYL-NORBORNAN-7-ONES - THE ROLE OF THROUGH-SPACE ELECTROSTATIC INTERACTIONS, Journal of the Chemical Society. Perkin transactions. I, (22), 1996, pp. 2665-2667
Experimental diastereoselectivities in hydride reduction of 2-endo-ary
lnorbornan-7-ones and computed transition state energetics reveal that
the facial selectivity in these systems is predominantly determined b
y repulsions between the approaching nucleophile and the electron clou
d of the aryl ring.