Facile synthetic route to enantiopure unsymmetric cis-2,5-disubstituted pyrrolidines |
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Authors: | Wang Ping-An Xu Zheng-Shuang Chen Chun-Feng Gao Xu-Guang Sun Xiao-Li Zhang Sheng-Yong |
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Institution: | Department of Pharmacy, Fourth Military Medical University, Xi'an 710032, China. |
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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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Keywords: | enantiopure cis‐2 5‐disubstituted pyrrolidine chiral auxiliary Grignard reaction X‐ray crystallographic analysis hydrogenolysis |
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