Preparation of Homochiral Azophenolic Crown Ethers Containing 1-Phenylethane-1,2-diol and 2,4,-Dimethyl-3-oxapentane-1,5-diol as a Chiral Subunit: Enantiomer Recognition Behavior Towards Chiral 2-Aminoethanol Derivatives. -The enantiomerically pure crown ethers (VII)-(X) are synthesized. Ether (VII
Preparation of homochiral azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
โ Scribed by Koichiro Naemura; Kazuko Ogasahara; Keiji Hirose; Yoshito Tobe
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 256 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0957-4166
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โฆ Synopsis
Enantiomerically pure azophenolic crown ethers 1--4 containing (S)-or (R)l-phenylethane-l,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-l,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-I showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives.
๐ SIMILAR VOLUMES
Crown ethers 1--6 containing two chiral subunits derived from (S)-Iphenylethane-l,2-diol and a phenol moiety bearing an intra-annular OH group and an additional para-substituent have been prepared in enantiomerically pure forms and their enantiomer recognition behaviour in complexation with neutral
Homochiral l-(l-adamantyl)ethane-l,Zdiol(5) was prepared and 1t.s absolute configuration was determined to be (q-(+)-5 by enzymatic and 'H n.m.r. spectroscopic methods. Using (s)-(+)-5 as a chual subunit, the homochiral crown ether (+)-18 was K. NAEMURA et al. (23% yield), [a], +37.1 (acetone), mp 1