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  • Title: Facile synthetic route to enantiopure unsymmetric cis-2,5-disubstituted pyrrolidines.
    Author: Wang PA, Xu ZS, Chen CF, Gao XG, Sun XL, Zhang SY.
    Journal: Chirality; 2007 Jul; 19(7):581-8. PubMed ID: 17508396.
    Abstract:
    The (+/-)-cis-5-arylcarbamoyl-2-ethoxycarbonylpyrrolidines 6a-g were firstly synthesized in 53-64% yields by using meso-diethyl-2,5-dibromoadipate 3 and (S)-(-)-1-phenylethylamine in three steps. The diastereomeric mixture (S;2S,5R)-(-)-7 and (S;2R,5S)-(+)-8 were prepared by the Grignard reaction and separated by a flash column chromatography in 29 and 52% yields. The absolute configurations of (+)-8 was confirmed by X-ray crystallographic analysis and the enantiopure pyrrolidines (2S,5R)-(-)-9/(2R,5S)-(+)-9 and (2S,5R)-(-)-10/(2R,5S)-(+)-10 were obtained in good yields.
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