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 |
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Authors: | Má tyá s Czugler,Petros P. Korkas,Petra Bombicz,Wilhelm Seichter,Edwin Weber |
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Abstract: | 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 (+)-2α-ethynyl-2β-hydroxybornane (4) or (+)-2α-ethynyl-2β-hydroxyfenchane (5) with 9,10-dibromoanthracene. Host compounds 1 and 2 from 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. Chirality 9:203–210, 1997. © 1997 Wiley-Liss, Inc. |
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Keywords: | chiral selectors natural product derived hosts optically active hosts clathrate hosts bulky diols inclusion compounds host-guest complexes chiroselective cocrystallization crystal packing analysis |
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