Chiral separation machinery using new crystalline inclusion hosts: Match/mismatch in the enantiomer recognition of (R,S)-1-methoxy-2-propanol effected by a borneol/fenchol building block exchange in the host molecule
✍ Scribed by Mátyás Czugler; Petros P. Korkas; Petra Bombicz; Wilhelm Seichter; Edwin Weber
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 258 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
New chiral host molecules 1 and 2 involving a bulky terpenoid unit and aromatic ethyne spacer groups were synthesized using Pd-catalyzed cross-coupling reactions of (+)-2␣-ethynyl-2-hydroxybornane (4) or (+)-2␣-ethynyl-2-hydroxyfenchane (5) with 9,10-dibromoanthracene. Host compounds 1 and 2 form crystalline inclusions with 1-methoxy-2-propanol (3) in 1:1 and 1:2 stoichiometry, respectively. In the case of 1, complete enantiomer resolution (ee > 99%) of 3 is effected in one cocrystallization step. However, constitutional isomer 2 failed in the enantiomer separation of 3, which might be explained due to the different crystal lattice buildup of these cocrystals.