Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2007(3): 0249-0249
DOI: 10.1055/s-2007-968262
DOI: 10.1055/s-2007-968262
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Enantiopure (S)- and (R)-α-Trifluoromethyl Proline
G. Chaume, M.-C. Van Severen, S. Marinkovic, T. Brigaud*
Université de Cergy-Pontoise, France
Further Information
Publication History
Publication Date:
20 February 2007 (online)
Significance
A convenient route to enantiopure α-trifluoromethyl proline is reported. Lewis acid catalyzed allylation of an easily accessible oxazolidinone derived from (R)-phenylglycinol generates a morpholin-2-one derivative in 86-92% yields as a diastereomeric mixture (dr = 69:31 to 75:25), independent of the diastereomeric ratio of the educt. Following PTSA-catalyzed lactonization, hydroboration, and mesylation, the pyrrolidine lactone is obtained as a diastereomeric mixture which may be separated by column chromatography. Standard hydrogenolysis affords both enantiomers of trifluoromethyl proline in five steps and up to 36% overall yield.