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Chemo‐Enzymatic Dynamic Kinetic Resolution of Symmetric and Non‐Symmetric α‐Hydroxy Ketones for Industrial Application
Author(s) -
PetrenzBeck Annika,
Kühn Jasmin,
Zuhse Ralf,
AnsorgeSchumacher Marion B.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900740
Subject(s) - kinetic resolution , benzoin , racemization , chemistry , pseudomonas stutzeri , enantiomeric excess , enantiomer , stereoselectivity , candida antarctica , lipase , catalysis , organic chemistry , enantioselective synthesis , transesterification , enzyme , bacteria , biology , genetics
α‐Hydroxy ketones are important intermediates in various drugs and fine chemicals. Stereoselective synthesis of both symmetric and asymmetric compounds is demonstrated involving benzoin, 2–2’‐furoin, phenylacetyl carbinol (PAC) and 2‐hydroxy‐1‐phenylpropan‐1‐one (HPP) as representatives. Dynamic kinetic resolution of the racemic preparations was achieved in one‐pot combining transesterification catalyzed by immobilized lipases from Pseudomonas stutzeri and Pseudozyma antarctica , respectively, and racemization mediated by the heterogeneous chemo‐catalyst Zr‐TUD‐1 in water‐free organic solvent. ( S )‐benzoin, ( S )‐2,2’‐furoin, ( S )‐PAC and ( R )‐HPP were obtained with both high efficiency and high enantiomeric excess. Within 90 minutes, 2,45 g ( S )‐PAC butyrate (ee 88%) yielded from a 130 mL batch reaction demonstrating both technical feasibility and relevance for application.