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

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.
Author Agnieszka Górska ZChF
Agnieszka Górska,,
- Department Of Physical Chemistry
, Halina Hajmowicz LPT
Halina Hajmowicz,,
- Laboratory Of Technological Processes
, Tomasz Kliś ZChF
Tomasz Kliś,,
- Department Of Physical Chemistry
, Janusz Serwatowski ZChF
Janusz Serwatowski,,
- Department Of Physical Chemistry
, Ludwik Synoradzki LPT
Ludwik Synoradzki,,
- Laboratory Of Technological Processes
Journal seriesApplied Organometallic Chemistry, ISSN 0268-2605 [1099-0739]
Issue year2011
Vol25
No4
Pages294–297
Keywords in English(acyloxy)boranes, Boronic acids, malic acid, tartaric acid
DOIDOI:10.1002/aoc.1757
URL http://onlinelibrary.wiley.com/doi/10.1002/aoc.1757/abstract
Languageen angielski
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b553fe8541935a0096aaea8d24b3a341ba08d35e0b4aeaa1283c363c9bdafd9c.pdf 176.69 KB
Score (nominal)30
Publication indicators WoS Impact Factor: 2011 = 2.061 (2) - 2011=1.849 (5)
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