Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid |
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| Institution: | 1. National Institute of Agrobiological Sciences, 1-2 Owashi, Tsukuba, Ibaraki 305-8634, Japan;2. National Food Research Institute, 2-1-12 Kannondai, Tsukuba, Ibaraki 305-8642, Japan;1. Instituto de Química, Universidade Federal de Uberlândia, Av. João Naves de Ávila, 2121, 38408100 Uberlândia, MG, Brazil;2. Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, 05508500 São Paulo, SP, Brazil;1. Institute of Bioelectronics (ICS-8/PGI-8), Forschungszentrum Jülich GmbH, Wilhelm-Johnen-Straße, 52425 Jülich, Germany;2. Institute of Materials in Electrical Engineering 1, RWTH Aachen University, Sommerfeldstrasse 24, 52074 Aachen, Germany;1. Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran;2. Institute of Physics of the Czech Academy of Sciences, Na Slovance 2, 182 21 Prague 8, Czech Republic;2. Institute of Organic Synthesis, UB RAS, 22, S. Kovalevskaya str., Ekaterinburg, 620041, Russia |
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| Abstract: | Enantioresolution of 3-octanol, 6-methyl-5-hepten-2-ol (sulcatol), and 1-octen-3-ol was conducted using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid) and (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid). In each case, the diastereomeric esters obtained were readily separated by HPLC. The stereochemistry of the esters could be assigned from their respective 1H NMR analyses. Solvolyses of the esters gave enantiopure alcohols and acids. MαNP and M9PP acids displayed almost equivalent properties in 1H NMR anisotropy. The chiral resolving ability of M9PP acid was slightly superior to that of MαNP acid in HPLC. |
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