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Water soluble lanthanoid benzoate complexes for the kinetic separation of cis/trans-limonene oxide

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Andrews, P.
Blair, M.
Fraser, B.
Junk, P.
Massi, Massimiliano
Tuck, K.
Date
2006
Type
Journal Article

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Andrews, Philip C. and Blair, Michael and Fraser, Benjamin H. and Junk, Peter C. and Massi, Massimiliano and Tuck, Kellie L.. 2006. Water soluble lanthanoid benzoate complexes for the kinetic separation of cis/trans-limonene oxide. Tetrahedron: Asymmetry 17 (19): pp. 2833-2838.
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Tetrahedron: Asymmetry
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Abstract

A new class of water soluble, environmentally friendly, lanthanoid 3,5-diacetamidobenzoate complexes (Ln = La, Gd, Yb) have been synthesized. The La and Gd complexes selectively catalyse hydrolysis of the cis-isomer of limonene oxide allowing for the separation of the trans-isomer (> 98:2 dr) in up to 74% yield. Comparative studies with the corresponding chlorides and triflates reveal the lanthanoid benzoate complexes to be more active than the chlorides, but less active, though more selective, than the triflates