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Highly diastereoselactive synthesis of chimeras of proline and glutamate

✍ Scribed by Konstantin V. Kudryavtsev; Mikhail Yu. Tsentalovich; Anton S. Yegorov; Eugene L. Kolychev

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
448 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Azomethine ylides have been generated from aromatic aldimines of α‐amino acid methyl esters under treatment with LiBr/Et~3~N and trapped with tert‐butyl acrylate yielding racemic orthogonally protected cis‐5‐arylpyrrolidine‐2,4‐dicarboxylates regio‐ and stereo‐selectively in high yields. Subsequent N‐methylation and deprotection of 4‐carboxylic group of cycloaddition products led to novel prolineglutamate cis‐chimeras with substituents at 2 and 5 positions of pyrrolidine scaffold.

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