Chemija / Chemistry
 ISSN 0235-7216 ISSN 2424-4538 (online) |
2012 m. Nr. 4 Synthesis of chiral bicyclo[3.3.1]nonane derivative as ionic liquid and using it for asymmetric Michael’s addition reaction
In this study a chiral bicyclo[3.3.1]nonane derivative as an ionic liquid was synthesized starting from (+)-(1S,5S)-bicyclo[3.3.1]nonane-2,6-dione (1a). Resulting compound (+)-(1S,2R,5S,6R)-2,6-di{[(N-methylimidazol-3-ium-3-yl]acetyl) oxy} bicyclo [3.3.1]nonane di(tetrafluoroborate) (4) was used as a chiral catalyst for the asymmetric Michael’s addition reaction of 1,3-diphenyl-2-propen-1-one (chalcone 5) with diethyl malonate. In that case (+)-(S)-diethyl-2-(3-oxo-1,3-diphenylpropyl) malonate (7) was obtained. Optical purity of purposive compound 7 was 57%, the enantiomeric excess calculated according to spectral data (1H NMR) ee = 35%. This difference can be explained by the Horeau effect.
Keywords: bicyclo[3.3.1]nonane, chiral ionic liquid, imidazolium cation, asymmetric Michael’s addition reaction |
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