A study of the formation and application of new chiral water soluble lanthanoid benzoates using real-time infrared spectroscopy |
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| Authors: | Philip C Andrews Benjamin H Fraser William J Gee David Giera Peter C Junk Massimiliano Massi Kellie L Tuck |
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| Institution: | 1. School of Chemistry, Monash University, Clayton, Victoria 3800, Australia;2. The Scripps Research Institute, 10550 North Torrey Pines Road La Jolla, California 92037, United States |
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| Abstract: | A range of water soluble lanthanoid benzoate complexes of composition Ln(Bz)3(H2O)n] (Ln = La, Gd, Ho and Yb; Bz = 3,5-bis((R)-2,3-dihydroxypropoxy)benzoate and 3,4,5-tris((R)-2,3-dihydroxypropoxy)benzoate) have been prepared by reaction of lanthanoid bicarbonates with three equivalents of the corresponding optically active benzoic acid in water. Application of Ln(Bz)3(H2O)n] as asymmetric catalysts for epoxide ring opening reactions has been investigated using styrene oxide, showing complete conversion after 20 h, albeit with no significant enantiomeric excess observed. The formation of the lanthanoid complexes and subsequent catalytic conversion of styrene oxide to phenylethane-1,2-diol were monitored using real-time infrared (RTIR) spectroscopy, yielding information about reaction pathways and intermediates. |
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| Keywords: | Lanthanoid Rare earth Carboxylates In situ IR Ring-opening |
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