Novel Synthesis of 1-Cyanocyclopropane-1-carboxylic Acid and Its Application to the Synthesis of Amino Acids Containing Cyclopropane Rings

Abstract

1-Cyano-1-trimethylsilylcyclopropanes 1 were efficiently converted to 1-cyanocyclopropane-1-carboxylic acids (2) in the presence of a fluoride ion source under a carbon dioxide atmosphere. This transformation provides a novel route to 1-aminocyclopropane-1-carboxylic acid (ACC), which is found in many plants, and to its homolog 7 (1-aminomethylcyclopropane-1-carboxylic acid).