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
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
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
.