Resolution of (S,S)-4-(2,2,4-trimethylchroman-4-yl)phenyl camphanate and its 4-chromanyl epimer by crystallization

Catharine Esterhuysen, Martin W Bredenkamp, Gareth O Lloyd

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Abstract

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.

Original languageEnglish
Pages (from-to)O32-O34
Number of pages3
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume61
Issue number1
DOIs
Publication statusPublished - Jan 2005

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