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Enantioselective Reduction of 3‐Aryl‐2‐oxo‐propanoic Acids: A Comparison of Enzymatic and Transition‐Metal‐Catalyzed Methods
Author(s) -
Lüttenberg Sebastian,
Ta Tien Dat,
von der Heyden Jan,
Scherkenbeck Jürgen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201506
Subject(s) - enantioselective synthesis , chemistry , catalysis , aryl , propanoic acid , enzyme , organic chemistry , substrate (aquarium) , combinatorial chemistry , stereochemistry , alkyl , oceanography , geology
Phenyllactic acids are important constituents of depsipeptides, which are a large class of natural products expressing a wide range of biological activities. Despite there being several methods for the enantioselective synthesis of α‐hydroxy acids, almost no studies are available addressing the substrate selectivity of transition‐metal and enzyme‐catalyzed methods for the preparation of substituted phenyllactic or more general aryllactic acids. We report herein comparative results for Rh‐DiPAMP (DiPAMP = 1,2‐ethandiylbis[( o ‐methoxyphenyl)phenylphosphane]) and lactate dehydrogenase catalyzed enantioselective reductions of several 3‐aryl‐2‐oxopropanoic acids.