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Enantiogroup‐Differentiating Biocatalytic Reductions of Prochiral C s ‐Symmetrical Dicarbonyl Compounds to meso Compounds
Author(s) -
Skoupi Marc,
Vaxelaire Carine,
Strohmann Carsten,
Christmann Mathias,
Niemeyer Christof M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500741
Subject(s) - desymmetrization , diastereomer , stereocenter , stereoselectivity , yield (engineering) , chemistry , biocatalysis , diol , stereochemistry , reduction (mathematics) , organic chemistry , enantioselective synthesis , catalysis , reaction mechanism , mathematics , materials science , metallurgy , geometry
The stereoselective reduction of symmetrical prochiral dicarbonyl compounds bearing enantiotopic carbonyl groups yields several stereogenic centers in one step. In a proof‐of‐concept study, a new approach is described for the enzymatic desymmetrization of 5‐nitrononane‐2,8‐dione via sequential biocatalytic reduction steps utilizing ketoreductases to yield all possible diastereomers of 5‐nitrononane‐2,8‐diol.