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Enantioselective Synthesis of ( R )‐2‐Arylpropanenitriles Catalysed by Ene‐Reductases in Aqueous Media and in Biphasic Ionic Liquid–Water Systems
Author(s) -
Brenna Elisabetta,
Crotti Michele,
Gatti Francesco G.,
Manfredi Alessia,
Monti Daniela,
Parmeggiani Fabio,
Santangelo Sara,
Zampieri Davila
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402205
Subject(s) - ionic liquid , enantioselective synthesis , nitrile , chemistry , substrate (aquarium) , ene reaction , aqueous solution , aqueous medium , organic chemistry , methylene , combinatorial chemistry , catalysis , oceanography , geology
Abstract The enantioselective reduction of α‐methylene nitrile derivatives catalysed by ene‐reductases affords the corresponding ( R )‐2‐arylpropanenitriles with high conversion values. The reaction is investigated either in aqueous medium (with an organic cosolvent or by loading the substrate onto hydrophobic resins) or in a biphasic ionic liquid–water system. The use of ionic liquids, herein with isolated ene‐reductases, is found to improve the work‐up and the substrate recovery method. The synthetic manipulation of the final chiral nitrile derivatives indicates how this biocatalysed method can be exploited for the preparation of a wide range of chiral compounds.