5‐Carboxymethyl‐2‐(4‐methylthiophenyl)‐1,3,2‐dioxaborolan‐4‐one: synthesis,characterization and application in enantioselective reduction of ketones |
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| Authors: | Agnieszka Górska Halina Hajmowicz Tomasz Kli? Janusz Serwatowski Ludwik Synoradzki |
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| Institution: | 1. Physical Chemistry Department, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00‐664 Warsaw, Poland;2. Laboratory of Technological Processes, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00‐664 Warsaw, Poland |
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| Abstract: | The reaction of arylboronic acids with L ‐O‐benzoyl‐tartaric acid and D ,L ‐malic acid has been studied. The obtained (acyloxy)boranes are moderately stable in solution and decompose to give boroxines. 5‐Carboxymethyl‐2‐(4‐methylthiophenyl)‐1,3,2‐dioxaborolan‐4‐one was obtained in the reaction of 4‐methylthiophenylboronic acid with D ,L ‐malic acid and characterized by X‐ray structural analysis. The use of L ‐(?)‐malic acid afforded the optically pure product which can be used as the powerful chiral reagent in the enantioselective reduction of ketones. Copyright © 2011 John Wiley & Sons, Ltd. |
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| Keywords: | (acyloxy)boranes boronic acids tartaric acid malic acid |
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