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

Barbara Mohar; Jérôme Baudoux; Jean-Christophe Plaquevent; Dominique Cahard

doi:10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO;2-B

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

Angew Chem Int Ed Engl. 2001 Nov 19;40(22):4214-4216. doi: 10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO;2-B.

Authors

Barbara Mohar¹, Jérôme Baudoux¹, Jean-Christophe Plaquevent¹, Dominique Cahard¹

Affiliation

¹ Université de Rouen UMR 6014 de l'IRCOF 76821 Mont Saint Aignan Cedex, France, Fax: (+33) 2-35-52-29-71.

PMID: 29712084
DOI: 10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO;2-B

Abstract

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].

Keywords: alkaloids; amino acids; asymmetric synthesis; fluorination; fluorine.