Electrophilic Fluorination Mediated by Cinchona Alkaloids: Highly Enantioselective Synthesis of α-Fluoro-α-phenylglycine Derivatives

A decisive step forward: A one‐step fluorination on modified cinchona alkaloids produced a new range of enantiopure fluorinating agents that display high enantioselectivities in electrophilic fluorination. The first enantioselective synthesis of N‐protected α‐fluorophenylglycine derivatives was achi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2001-11, Vol.40 (22), p.4214-4216
Main Authors: Mohar, Barbara, Baudoux, Jérôme, Plaquevent, Jean-Christophe, Cahard, Dominique
Format: Article
Language:English
Subjects:
alkaloids
amino acids
asymmetric synthesis
fluorination
fluorine
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Summary:A decisive step forward: A one‐step fluorination on modified cinchona alkaloids produced a new range of enantiopure fluorinating agents that display high enantioselectivities in electrophilic fluorination. The first enantioselective synthesis of N‐protected α‐fluorophenylglycine derivatives was achieved with an enantiomeric excess up to 94 % [Eq. (a); R=Et, CN; HMDS=hexamethyldisilazanide].
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO;2-B