FIGR ID=jo061939rn00001>figures/jo061939rn00001.gif" ALIGN="left" HSPACE=5> |
Comparison o
f the room- and low-temperat
ure 1H NMR spectra o
f the bis-(
R)- or bis-(
S)-MPA esterderivative o
f an open chain
sec,sec-1,2-diol allows the easy determination o
f its relative stereochemistryand in some cases absolute con
figuration. I
f the diol is anti, its absolute con
figuration can be directlydeduced
from the signs o
f fchars/Delta.gi
f" BORDER=0 >
fchars/delta.gi
f" BORDER=0 >
T1T2 for substituents R
1/R
2, but i
f the relative stereochemistry o
f the diol issyn, the assignment o
f its absolute con
figuration requires the preparation o
f two derivatives (both thebis-(
R)- and bis-(
S)-MPA esters), comparison o
f their room-temperat
ure 1H NMR spectra, and calculationo
f the
fchars/Delta.gi
f" BORDER=0 >
fchars/delta.gi
f" BORDER=0 >
RS signs
for the methines H
fchars/alpha.gi
f" BORDER=0>(R
1) and H
fchars/alpha.gi
f" BORDER=0>(R
2) and R
1/R
2 protons. The reliability o
f thesecorrelations is validated with 17 diols o
f known absolute con
figuration used as model compounds.