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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.