Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: a short route to γ-aminobutyric acid esters

Michael R Emmett; Huck K Grover; Michael A Kerr

doi:10.1021/jo3010606

Tandem ring-opening decarboxylation of cyclopropane hemimalonates with sodium azide: a short route to γ-aminobutyric acid esters

J Org Chem. 2012 Aug 3;77(15):6634-7. doi: 10.1021/jo3010606. Epub 2012 Jul 16.

Authors

Michael R Emmett¹, Huck K Grover, Michael A Kerr

Affiliation

¹ Department of Chemistry, Western University, London, Ontario, Canada N6A 5B7.

PMID: 22775774
DOI: 10.1021/jo3010606

Abstract

Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce γ-azidobutyric acids in good yields. These adducts were hydrogenated to form γ-aminobutyric acid (GABA) methyl esters.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclopropanes / chemistry*
Decarboxylation
Molecular Structure
Sodium Azide / chemistry*
gamma-Aminobutyric Acid / analogs & derivatives
gamma-Aminobutyric Acid / chemical synthesis
gamma-Aminobutyric Acid / chemistry

Substances

Cyclopropanes
4-aminobutyric acid methyl ester
gamma-Aminobutyric Acid
Sodium Azide