Enantiomerically Pure (R)- and (S)-15-Hydroxy[2.2]paracyclophane-4-carbaldehyde (iso-FHPC): A Novel Parent Compound for Planar Chiral Ligands

The planar chiral 15‐hydroxy[2.2]paracyclophane‐4‐carbaldehyde (2, iso‐FHPC) was synthesized and resolved via its Schiff bases 8 by using the enantiomers of α‐phenylethylamine. The absolute configurations of the enantiomers of 2 were determined by a combined X‐ray diffraction and chemical correlatio...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-06, Vol.2003 (11), p.2056-2061
Main Authors: Rozenberg, Valeria I., Antonov, Dmitrii Yu, Sergeeva, Elena V., Vorontsov, Evgenii V., Starikova, Zoya A., Fedyanin, Ivan V., Schulz, Christian, Hopf, Henning
Format: Article
Language:English
Subjects:
Absolute configuration determination
Cyclophanes
N,O‐ligands
O-ligands
Planar chirality
Resolution into enantiomers
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Summary:The planar chiral 15‐hydroxy[2.2]paracyclophane‐4‐carbaldehyde (2, iso‐FHPC) was synthesized and resolved via its Schiff bases 8 by using the enantiomers of α‐phenylethylamine. The absolute configurations of the enantiomers of 2 were determined by a combined X‐ray diffraction and chemical correlation study. Derivatives 9, the first representatives of cyclophane‐derived aminophenols with a pseudo‐gem arrangement of the functional groups were synthesized. All new chiral compounds can be regarded as prospective ligands for asymmetric synthesis and catalysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200200670