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Enantioselective Oxidative Aerobic Dealkylation of N ‐Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme
Author(s) -
Gandomkar Somayyeh,
Fischereder EvaMaria,
Schrittwieser Joerg H.,
Wallner Silvia,
Habibi Zohreh,
Macheroux Peter,
Kroutil Wolfgang
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507970
Subject(s) - enantioselective synthesis , chemistry , alkylation , berberine , enantiomer , enzyme , organic chemistry , stereochemistry , catalysis
N‐Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N‐dealkylation has not been yet reported. In this study, exclusively the ( S )‐enantiomers of racemic N ‐ethyl tertiary amines (1‐benzyl‐ N ‐ethyl‐1,2,3,4‐tetrahydroisoquinolines) were dealkylated to give the corresponding secondary ( S )‐amines in an enantioselective fashion at the expense of molecular oxygen. The reaction is catalyzed by the berberine bridge enzyme, which is known for CC bond formation. The dealkylation was demonstrated on a 100 mg scale and gave optically pure dealkylated products ( ee >99 %).