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Dynamic Kinetic Resolution of rac ‐2‐Hydroxy‐1‐indanone by using a Heterogeneous Ru(OH) 3 /Al 2 O 3 Racemization Catalyst and Lipase
Author(s) -
Långvik Otto,
Saloranta Tiina,
Kirilin Alexey,
Liljeblad Arto,
MäkiArvela Päivi,
Kanerva Liisa T.,
Murzin Dmitry Yu.,
Leino Reko
Publication year - 2010
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.201000161
Subject(s) - racemization , kinetic resolution , lipase , chemistry , catalysis , resolution (logic) , ruthenium , kinetic energy , organic chemistry , enantioselective synthesis , enzyme , artificial intelligence , computer science , physics , quantum mechanics
Kinetic resolution and dynamic kinetic resolution, in particular, provide practical tools for synthesis of enantiomerically pure compounds. In the present work, the resolution of rac ‐2‐hydroxy‐1‐indanone and racemization of ( S )‐2‐hydroxy‐1‐indanone were investigated. Immobilized lipase AK ( Pseudomonas fluorescens ) was found as the best enzyme catalyst for kinetic resolution and ruthenium supported on Al 2 O 3 as a potential heterogeneous catalyst for racemization of the starting material. By combining the two reactions, a simple dynamic kinetic resolution of rac ‐2‐hydroxy‐1‐indanone producing ( R )‐1‐oxo‐indan‐2‐yl butanoate was developed. Under optimal conditions, the product was obtained in 92 % ee at approximately 90 % conversion.