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Asymmetric Synthesis of ( S )‐2‐Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis
Author(s) -
de Lange Ben,
Hyett David J.,
Maas Peter J. D.,
Mink Daniel,
van Assema Friso B. J.,
Sereinig Natascha,
de Vries André H. M.,
de Vries Johannes G.
Publication year - 2011
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.201000435
Subject(s) - biocatalysis , enantiopure drug , catalysis , chemistry , kinetic resolution , enantioselective synthesis , organic chemistry , combinatorial chemistry , phenylalanine , indole test , homogeneous , ring (chemistry) , stereochemistry , condensation , green chemistry , amino acid , reaction mechanism , biochemistry , physics , thermodynamics
A tale of two catalysts: ( S )‐2‐Indolinecarboxylic acid, an intermediate for ACE inhibitors, was until recently produced by Fischer indole synthesis and classical resolution in seven steps. However, Perkin condensation to form ortho ‐chlorocinnamic acid, which is converted to ( S )‐ ortho ‐chlorophenylalanine using the enzyme phenylalanine ammonia lyase prior to copper‐catalyzed ring closure thereof delivers the enantiopure product in just three steps.