A cationic ruthenium complex for the dynamic kinetic resolution of secondary alcohols

• Published in: Chemistry - A European Journal
• Main Authors: Fernandez-Salas, Jose A, Manzini, Simone, Nolan, Steven
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2014
• Subjects: Chemistry; dynamic kinetic resolution; enzyme catalysis; metal catalysis; racemization; ruthenium; CATALYTIC RACEMIZATION; ASYMMETRIC TRANSFORMATIONS; ENZYMATIC RESOLUTION; AMBIENT-TEMPERATURE; CHIRAL ACETATES; ENOL ACETATES; LIPASE; KETONES; ENZYMES; Antarc*; Antarctica
• Online Access: https://biblio.ugent.be/publication/8168444; http://hdl.handle.net/1854/LU-8168444; https://doi.org/10.1002/chem.201404096

A synthetic protocol making use of a well-defined cationic ruthenium complex 2 enabling the racemization of enantiomerically pure secondary alcohols in the presence of a weak base (K2CO3) is described. The compatibility of 2 with Candida Antarctica lipase B (Novozym 435) allows the development of an efficient dynamic kinetic resolution of sec-alcohols in the absence of an additional strong base. This procedure involves the first example of a dynamic kinetic resolution of alcohols in the presence of a cationic ruthenium catalyst. In addition, we describe the conversion of ketones to the enantioenriched acetates in a one-pot reaction, probing the versatility of complex 2.