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Facile synthetic route to enantiopure unsymmetric cis ‐2,5‐disubstituted pyrrolidines
Author(s) -
Wang PingAn,
Xu ZhengShuang,
Chen ChunFeng,
Gao XuGuang,
Sun XiaoLi,
Zhang ShengYong
Publication year - 2007
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20424
Subject(s) - enantiopure drug , chemistry , diastereomer , chirality (physics) , column chromatography , stereochemistry , grignard reaction , organic chemistry , enantioselective synthesis , catalysis , reagent , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
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 ;2 S ,5 R )‐(−)‐7 and ( S ;2 R ,5 S )‐(+)‐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 (2 S ,5 R )‐(−)‐9/(2 R ,5 S )‐(+)‐9 and (2 S ,5 R )‐(−) ‐ 10/(2 R ,5 S )‐(+)‐10 were obtained in good yields. Chirality, 2007. © 2007 Wiley‐Liss, Inc.
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