5‐Carboxymethyl‐2‐(4‐methylthiophenyl)‐1,3,2‐dioxaborolan‐4‐one: synthesis, characterization and application in enantioselective reduction of ketones | Zendy

Górska Agnieszka | Zendy; Hajmowicz Halina | Zendy; Kliś Tomasz | Zendy; Serwatowski Janusz | Zendy; Synoradzki Ludwik | Zendy

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5‐Carboxymethyl‐2‐(4‐methylthiophenyl)‐1,3,2‐dioxaborolan‐4‐one: synthesis, characterization and application in enantioselective reduction of ketones

Author(s) -

Górska Agnieszka,

Hajmowicz Halina,

Kliś Tomasz,

Serwatowski Janusz,

Synoradzki Ludwik

Publication year - 2011

Publication title -

applied organometallic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.53

H-Index - 71

eISSN - 1099-0739

pISSN - 0268-2605

DOI - 10.1002/aoc.1757

Subject(s) - chemistry , malic acid , tartaric acid , enantioselective synthesis , reagent , boranes , organic chemistry , medicinal chemistry , catalysis , citric acid , boron

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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