| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349511 | Tetrahedron: Asymmetry | 2006 | 6 Pages |
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.
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(+)-trans-Limonene oxideC10H16OEe 98%[α]D = +78 (neat)Source of chirality: kinetic separation of commercially available diastereoisomersAbsolute configuration: (1S,2R,4R)
