TY - JOUR
T1 - A study of the formation and application of new chiral water soluble lanthanoid benzoates using real-time infrared spectroscopy
AU - Andrews, Philip Craig
AU - Fraser, Benjamin Hugh
AU - Gee, William James
AU - Giera, David
AU - Junk, Peter Courtney
AU - Massi, Massimiliano
AU - Tuck, Kellie Louise
PY - 2010
Y1 - 2010
N2 - 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. (C) 2010 Elsevier Ltd. All rights reserved.
AB - 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. (C) 2010 Elsevier Ltd. All rights reserved.
UR - http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TH8-4YDT42P-3&_user=542840&_coverDate=05%2F10%2F2010&_rdoc=1&_fmt=high&_orig=search&_sort=d
U2 - 10.1016/j.poly.2010.02.024
DO - 10.1016/j.poly.2010.02.024
M3 - Article
SN - 0277-5387
VL - 29
SP - 1764
EP - 1770
JO - Polyhedron
JF - Polyhedron
IS - 7
ER -