Chi
ral GC sepa
ration o
f (±)-2-allyl-2-ca
rboethoxycyclopentanone (
9) and the alcohols (±)-3-(hyd
roxymethyl)-5-ca
rboethoxy-2-oxabicyclo[3.3.0]octane (
7), (±)-2-allyl-2-ca
rboethoxycyclopentanol (
8), and thei
r acetylated andt
ri
fluo
roacetylated de
rivatives we
re investigated on th
reede
rivatized
fcha
rs/beta2.gi
f" BORDER=0 ALIGN="middle">-cyclodext
rins (CDs) diluted in SE-54 o
r1701-OH: 2,3,6-t
ri-O-methyl-
fcha
rs/beta2.gi
f" BORDER=0 ALIGN="middle">-CD (PMCD); 2,3-di-
O-methyl-6-
O-(
tert-butyldimethylsilyl)-
fcha
rs/beta2.gi
f" BORDER=0 ALIGN="middle">-CD (DIMETBCD);2,3-di-
O-acetyl-6-
O-(
tert-butyldimethylsilyl)-
fcha
rs/beta2.gi
f" BORDER=0 ALIGN="middle">-CD (DIACTBCD). The unde
rstanding o
f these chi
ral sepa
rationsis ext
remelly
relevant, since cyclopentanic and bicycliccyclopentanic
rings a
re common st
ructu
ral
featu
res o
fmany impo
rtant natu
ral p
roducts and new pha
rmaceuticald
rugs. In gene
ral DIMETBCD diluted in SE-54 showedthe best chi
ral
resolution to alcohols
7 and
8 and onlyDIACTBCD showed enantioselectivity to
9. Hyd
rogenbonds p
rediction and dipole moments data we
re obtainedby molecula
r modeling calculations
fo
r 7ab and
8ab andAc and TFA de
rivatives. Compa
rison o
f these data withthe ch
romatog
raphic pa
ramete
rs
fo
r the
related compounds we
re used to explain the di
ffe
rences o
f thei
relution o
rde
rs and diaste
reo- and enantiome
ric sepa
rations on the above chi
ral stationa
ry phases (CSPs). The
results suggest that the CSPs enantioselectivities a
re nota
ffected by the ca
rboethoxy-
functionalized cyclopentanicand bicyclic cyclopentanic
rings themselves but mainlyby the
functional g
roup on the othe
r ste
reogenic cente
r.