Premium
Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron‐Catalyzed Hydrogenation–Racemization and Enzymatic Resolution Cascade
Author(s) -
ElSepelgy Osama,
Brzozowska Aleksandra,
Rueping Magnus
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700169
Subject(s) - racemization , acylation , chemistry , catalysis , cascade , organic chemistry , biocatalysis , kinetic resolution , asymmetric hydrogenation , enzyme catalysis , combinatorial chemistry , enantioselective synthesis , reaction mechanism , chromatography
A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation–dehydrogenation–hydrogenation of prochiral ketones. By merging the iron‐catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones, as well as diketones, were reductively acylated. The corresponding products were isolated with high yields and enantioselectivities. The use of an iron catalyst together with molecular hydrogen as the hydrogen donor and readily available ethyl acetate as acyl donor make this cascade process highly interesting in terms of both economic value and environmental credentials.