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Oxime ethers as potential juvenoids: Synthesis of optical isomers
Author(s) -
Wimmer Zdenêk,
Vašíčková Soňa,
Šaman David,
Romaňuk Miroslav
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001159
Subject(s) - chemistry , enantiomer , oxime , molecule , chiral column chromatography , proton nmr , stereochemistry , chiral derivatizing agent , carbon 13 nmr , nmr spectra database , organic chemistry , spectral line , physics , astronomy
Two racemic juvenoids 5 and 6 and their optical isomers 10 , 11 , 17 and 18 having chiral centres in the aliphatic side chain were synthetized. The second chiral centre in the molecules remained racemic in all derivatives prepared. The absolute configurations of the optically active centres of the enantiomers were determined on the basis of the 1 H‐NMR spectral evaluation of the diastereoisomeric MTPA esters 12 , 13 , 19 and 20 derived from the intermediate alcohols 8 and 15 . The optical purity was established by an HPLC analysis of the corresponding MTPA esters. The 1 H‐NMR spectra of all compounds as well as the CD spectra of all chiral isomers were measured and discussed.