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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
Author(s) -
Czugler Mátyás,
Korkas Petros P.,
Bombicz Petra,
Seichter Wilhelm,
Weber Edwin
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:3<203::aid-chir1>3.0.co;2-g
Subject(s) - chemistry , enantiomer , chirality (physics) , stoichiometry , inclusion compound , molecule , stereochemistry , isomerization , crystal structure , crystallography , organic chemistry , catalysis , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
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.