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

M. Czugler, Petros P. Korkas, P. Bombicz, Wilhelm Seichter, Edwin Weber

Research output: Contribution to journalArticle

11 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)203-210
Number of pages8
JournalChirality
Volume9
Issue number3
DOIs
Publication statusPublished - 1997

Fingerprint

propylene glycol methyl ether
Acetylene
Enantiomers
Terpenes
Cross Reactions
Propanol
Machinery
Crystalline materials
Molecules
Crystal lattices
Stoichiometry
Isomers
isoborneol
fenchol

Keywords

  • bulky diols
  • Chiral selectors
  • chiroselective cocrystallization
  • clathrate hosts
  • crystal packing analysis
  • host-guest complexes
  • inclusion compounds
  • natural product derived hosts
  • optically active hosts

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

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title = "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",
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 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.",
keywords = "bulky diols, Chiral selectors, chiroselective cocrystallization, clathrate hosts, crystal packing analysis, host-guest complexes, inclusion compounds, natural product derived hosts, optically active hosts",
author = "M. Czugler and Korkas, {Petros P.} and P. Bombicz and Wilhelm Seichter and Edwin Weber",
year = "1997",
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AU - Czugler, M.

AU - Korkas, Petros P.

AU - Bombicz, P.

AU - Seichter, Wilhelm

AU - Weber, Edwin

PY - 1997

Y1 - 1997

N2 - 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 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.

AB - 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 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.

KW - bulky diols

KW - Chiral selectors

KW - chiroselective cocrystallization

KW - clathrate hosts

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KW - host-guest complexes

KW - inclusion compounds

KW - natural product derived hosts

KW - optically active hosts

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