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Catalytic Asymmetric Mono‐Fluorination of α‐Keto Esters: Synthesis of Optically Active β‐Fluoro‐α‐Hydroxy and β‐Fluoro‐α‐Amino Acid Derivatives
Author(s) -
Suzuki Shoko,
Kitamura Yuki,
Lectard Sylvain,
Hamashima Yoshitaka,
Sodeoka Mikiko
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201201303
Subject(s) - enantioselective synthesis , optically active , catalysis , chemistry , amino acid , organic chemistry , combinatorial chemistry , biochemistry
Enantioselective mono‐fluorination of α‐keto esters was achieved using a mildly basic palladium μ‐hydroxo complex as catalyst. Subsequent one‐pot reduction afforded optically active β‐fluoro‐α‐hydroxy esters. These compounds were then converted into β‐fluoro‐α‐amino esters, which are potentially useful in medicinal chemistry research.