Stereoselective Synthesis of (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid via C–H Insertion of Alkylidenecarbene

Susumu OHIRA; Megumi AKIYAMA; Kumiko KAMIHARA; Yuichi ISODA; Atsuhito KUBOKI

doi:10.1271/bbb.66.887

Organic Chemistry Notes

Stereoselective Synthesis of (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid via C–H Insertion of Alkylidenecarbene

Susumu OHIRA, Megumi AKIYAMA, Kumiko KAMIHARA, Yuichi ISODA, Atsuhito KUBOKI

Author information

Keywords: metabotropic glutamate agonist, amino acid, chiral quaternary center, C–H insertion, alkylidenecarbene

JOURNAL FREE ACCESS

2002 Volume 66 Issue 4 Pages 887-891

DOI https://doi.org/10.1271/bbb.66.887

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Abstract

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C–H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.

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