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Synfacts 2008(6): 0559-0559  
DOI: 10.1055/s-2008-1072611
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (S,S)-Reboxetine

Contributor(s): Philip Kocienski
T.-X. Métro, D. Gomez Pardo*, J. Cossy*
Laboratoire de Chimie Physique, ESPCI, Paris, France
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

The Cossy group describes two syntheses of (S,S)-reboxetine. A mechanism for the key 1,2-N,O-transposition E→H (J. Cossy and coworkers Org. Lett. 2006, 8, 3509; J. Org. Chem. 2007, 72, 6556) is proposed that entails the formation of an aziridinium ion intermediate G that undergoes regioselective cleavage by trifluoroacetate ion with inversion of configuration.