Electrostatic and steric control of π-facial stereoselectivity in nucleophilic additions of LiH and MeLi to endo-5,6-disubstituted norbornen-7-ones: an ab initio MO study

Abstract

Fully optimized transition structures for the addition of LiH and MeLi to several endo-5,6-disubstituted norbornen-7-ones have been located at the HF/6-31G(d) level of theory; single point MP2/6-31G(d) energies, together with point charge calculations suggest that a combination of electrostatic and steric effects, and not hyperconjugative effects, control the π-facial stereoselectivity of LiH and MeLi additions.