Origin of pi-facial stereoselectivity in nucleophilic addition. Application of the exterior frontier orbital extension model to substituted bicyclo[2.2.1]heptan-7-ones

Authors
Tomoda, S Senju, T
Citation
S. Tomoda et T. Senju, Origin of pi-facial stereoselectivity in nucleophilic addition. Application of the exterior frontier orbital extension model to substituted bicyclo[2.2.1]heptan-7-ones, CHEM LETT, (4), 1999, pp. 353-354
Citations number
13
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
4
Year of publication
1999
Pages
353 - 354
Database
ISI
SICI code
0366-7022(199904):4<353:OOPSIN>2.0.ZU;2-H
Abstract
The exterior frontier orbital extension model (EFOE model) has shown that p i-facial stereoselection in nucleophilic additions of 2,3-endo,endo-disubst ituted bicyclo[2.2.1]heptan-7-ones (1) is dictated by the three terms of th e Salem-Klopman equation steric effect, electrostatic interaction and orbit al interaction.