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oai:kanazawa-u.repo.nii.ac.jp:00010782 2024-06-20T06:06:44Z 934:935:937

Desymmetrization of meso-methylenecyclopropanes by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction 藤波, 修平 猪股, 勝彦 宇梶, 裕 Yonezawa, Yasushi Furuya, Tomoki Aratani, Takahiro 10115272 Fujinami, Shuhei 50110599 Inomata, Katsuhiko 80193853 Ukaji, Yutaka Desymmetrization of various meso-methylenecyclopropanes was accomplished by a palladium-catalyzed asymmetric ring-opening bis(alkoxycarbonylation) reaction employing a chiral bioxazoline ligand. The reaction proceeded smoothly in the presence of copper(I) triflate under carbon monoxide and oxygen at ambient pressure to give the corresponding optically active α-methyleneglutarates with up to 60% ee. Desymmetrization of protected meso-(3-methylenecyclopropane- 1,2-diyl)dimethanols was also carried out to give enantioenriched highly oxygen-functionalized α-methyleneglutarates. © 2014 Elsevier Ltd. All rights reserved. Elsevier 2014-06-30 2017-10-03 eng journal article AM https://doi.org/10.24517/00010769 http://hdl.handle.net/2297/41334 https://kanazawa-u.repo.nii.ac.jp/records/10782 10.24517/00010769 10.1016/j.tetasy.2014.05.007 AA1074621X 0957-4166 Tetrahedron Asymmetry 25 12 936 943 https://kanazawa-u.repo.nii.ac.jp/record/10782/files/SC-PR-UKAJI-Y-936.pdf application/pdf 453.4 kB 2017-10-03