TY - JOUR
T1 - Resolution of (S,S)-4-(2,2,4-trimethylchroman-4-yl)phenyl camphanate and its 4-chromanyl epimer by crystallization
AU - Esterhuysen, Catharine
AU - Bredenkamp, Martin W
AU - Lloyd, Gareth O
PY - 2005/1
Y1 - 2005/1
N2 - Dianin's compound (4-p-hydroxyphenyl- 2,2,4-trimethylchroman) has been resolved by crystallization of the (S)-(-)-camphanic esters (S, S)- and (R, S)- 4-(2,2,4- trimethylchroman4- yl) phenyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1] heptane-1- carboxylate, both C28H32O5, from 2-methoxyethanol, yielding the pure S, S diastereomer. The relative stereochemistry of both diastereomers has been determined by X-ray crystallography, from which the absolute stereochemistry could be deduced from the known configuration of the camphanate moiety. The crystallographic conformations have been analysed, including the 1: 1 disorder of the R, S diastereomer.
AB - Dianin's compound (4-p-hydroxyphenyl- 2,2,4-trimethylchroman) has been resolved by crystallization of the (S)-(-)-camphanic esters (S, S)- and (R, S)- 4-(2,2,4- trimethylchroman4- yl) phenyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1] heptane-1- carboxylate, both C28H32O5, from 2-methoxyethanol, yielding the pure S, S diastereomer. The relative stereochemistry of both diastereomers has been determined by X-ray crystallography, from which the absolute stereochemistry could be deduced from the known configuration of the camphanate moiety. The crystallographic conformations have been analysed, including the 1: 1 disorder of the R, S diastereomer.
U2 - 10.1107/S0108270104029671
DO - 10.1107/S0108270104029671
M3 - Article
C2 - 15640588
SN - 0108-2701
VL - 61
SP - O32-O34
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
IS - 1
ER -