Origin of pi-facial diastereoselection in nucleophilic addition to 1,3-diheteran-5-ones (heteroatom = O, S). Theoretical evidence for the importance of ground-state effects

Authors
Tomoda, S Kaneno, D Senju, T
Citation
S. Tomoda et al., Origin of pi-facial diastereoselection in nucleophilic addition to 1,3-diheteran-5-ones (heteroatom = O, S). Theoretical evidence for the importance of ground-state effects, CHEM LETT, (11), 1999, pp. 1161-1162
Citations number
16
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
11
Year of publication
1999
Pages
1161 - 1162
Database
ISI
SICI code
0366-7022(199911):11<1161:OOPDIN>2.0.ZU;2-T
Abstract
The exterior frontier orbital extension model (the EFOE Model) strongly sug gested that reversal of pi-facial diastereoselection in nucleophilic additi ons of 1,3-diheteran-5-ones (heteroatom = O or S) may originate from the un ique ground-state conformation and the pi-facial difference in the LUMO ext ension around the carbonyl carbon rather than from transition state effects .