Synthesis of 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, a rigid non-chiral analogue of 2-aminoadipic acid

A non-chiral, rigid 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, an analogue of 2-aminoadipic acid, has been synthesized in six steps from dimethyl- meso-2,5-dibromohexanedioate in 28% total yield. A key step in the synthesis is double alkylation of a dimethyl pyrrolidine-2,5-dicarboxylate by 1...

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Bibliographic Details
Published in:Tetrahedron letters 2007-06, Vol.48 (23), p.4061-4063
Main Authors: Kubyshkin, Vladimir S., Mikhailiuk, Pavel K., Komarov, Igor V.
Format: Article
Language:English
Subjects:
Conformational restriction
Ester enolate alkylation
Non-natural amino acids
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Summary:A non-chiral, rigid 7-azabicyclo[2.2.1]heptane-1,4-dicarboxylic acid, an analogue of 2-aminoadipic acid, has been synthesized in six steps from dimethyl- meso-2,5-dibromohexanedioate in 28% total yield. A key step in the synthesis is double alkylation of a dimethyl pyrrolidine-2,5-dicarboxylate by 1-bromo-2-chloroethane.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.04.019