5-Carboxymethyl-2-(4-methylthiophenyl)-1,3,2-dioxaborolan-4-one: synthesis, characterization and application in enantioselective reduction of ketones
Agnieszka Górska , Halina Hajmowicz , Tomasz Kliś , Janusz Serwatowski , Ludwik Synoradzki
AbstractThe 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.
|Journal series||Applied Organometallic Chemistry, ISSN 0268-2605 [1099-0739]|
|Keywords in English||(acyloxy)boranes, Boronic acids, malic acid, tartaric acid|
|Publication indicators||: 2011 = 2.061 (2) - 2011=1.849 (5)|
|Citation count*||0 (2015-02-24)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.