PM3 calculations indicate that π-facial diastereoselection in the reaction between 2,3-endo-substituted 7-methylenenorbornanes and electrophiles such as Hg(OR)2 or I+ is determined by electrostatic asymmetry whereas the reaction with BH3 is controlled by orbital interactions.
H. B. Broughton, S. M. Green and H. S. Rzepa, J. Chem. Soc., Chem. Commun., 1992, 998 DOI: 10.1039/C39920000998
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