TY - JOUR
T1 - Synthesis of Highly Pure Enantiomers of the Insecticide Salithion
AU - Wu, Shao Yong
AU - Hirashima, Akinori
AU - Eto, Morifusa
AU - Yanagi, Kazunori
AU - Nishioka, Eriko
AU - Moriguchi, Koichi
N1 - Funding Information:
Acknowledgrnents. We thank Dr. M. Sasaki at the Takarazuka Institute of Sumitomo Chemical Co. for HPLC analyses of the salithion enantiomers. This work was supported in part by a Grant-in-Aid for Scientific Research from the Education, Science and Culture of Japan.
PY - 1989
Y1 - 1989
N2 - Optically active salithion (>98% e.e.) was obtained via an L-proline methyl ester derivative (PS), whose diastereomers were easily separated, with subsequent sulfuric acid-catalyzed methanolysis. The configuration of each diastereomeric PS was determined by NMR and single-crystal X-ray analysis. The optical purity of each PS and of the salithion enantiomers was measured by 1H-NMR and HPLC, respectively. The sulfuric acid-catalyzed methanolysis of PS to salithion was confirmed to have proceeded with an inversion of the configuration at the phosphorus atom by an experiment using model compounds.
AB - Optically active salithion (>98% e.e.) was obtained via an L-proline methyl ester derivative (PS), whose diastereomers were easily separated, with subsequent sulfuric acid-catalyzed methanolysis. The configuration of each diastereomeric PS was determined by NMR and single-crystal X-ray analysis. The optical purity of each PS and of the salithion enantiomers was measured by 1H-NMR and HPLC, respectively. The sulfuric acid-catalyzed methanolysis of PS to salithion was confirmed to have proceeded with an inversion of the configuration at the phosphorus atom by an experiment using model compounds.
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U2 - 10.1271/bbb1961.53.157
DO - 10.1271/bbb1961.53.157
M3 - Article
AN - SCOPUS:85007731982
SN - 0002-1369
VL - 53
SP - 157
EP - 163
JO - Agricultural and Biological Chemistry
JF - Agricultural and Biological Chemistry
IS - 1
ER -