Synthesis 2015; 47(04): 575-586
DOI: 10.1055/s-0034-1379457
paper
© Georg Thieme Verlag Stuttgart · New York

Flexible and Modular Syntheses of Enantiopure 5-cis-Substituted Prolinamines from l-Pyroglutamic Acid

Felix Prause
,
Johannes Kaldun
,
Benjamin Arensmeyer
,
Benedikt Wennemann
,
Benjamin Fröhlich
,
Dagmar Scharnagel
,
Matthias Breuning*
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Publikationsverlauf

Received: 12. September 2014

Accepted after revision: 23. Oktober 2014

Publikationsdatum:
27. November 2014 (online)


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Abstract

A wide range (25 examples) of 5-cis-substituted prolinamines is prepared in five to ten steps starting from cheap l-pyroglutamic acid. Three routes, differing mainly in the order of introduction of the substituents at the 5-cis position, the pyrrolidine nitrogen atom, and the exocyclic amino function, are successfully developed.

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