Electrostatic vs. orbital control in π-facial diasteroselection: a PM3 SCF-MO study of electrophilic reactivity in 7-methylenenorbornanes
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 998-1000
- https://doi.org/10.1039/c39920000998
Abstract
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.Keywords
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