Importance of orbital and electrostatic interactions in determining π-facial selectivities in nucleophilic additions to endo-substituted bicyclo[2.2.2]octan-2-ones
The diastereoselectivities in nucleophilic additions to bicyclo[2.2.2]octan-2-ones can be modulated by distal endo-substituents; both orbital and electrostatic interactions contribute to the observed stereoselectivity.