Application of a new methodology for the synthesis and resolution of a ß-(thien-2-yl) proline with the 7-azanorbornane skeleton

Abstract

The enantiomers of a heavily constrained proline derivative, methyl (1S,2R,4R)- and (1R,2S,4S)-2-(thien-2-yl)-7-azabicyclo [2.2.1]heptane-1-carboxylate, have been obtained separately by resolution of the racemic mixture using chiral high performance liquid chromatography. This is a particular example of the application of our new methodology, which takes advantage of the efficiency of chromatographic resolution techniques for the preparation of both enantiomers of a broad variety of proline–α-amino acid chimeras with a 7-azanorbornane skeleton.