A New and Convenient Preparation of 1-Aminocyclopropanecarboxylic Acid from Acrolein

Article abstract of DOI:10.1021/jo00301a013

Cyclopropanecarboxylic acid 3 and cyclopropanone hemiacetal 4 have been tested as possible convenient precursors of the α-aminocyclopropanecarboxylic acid (1), an immediate biosynthetic source of ethylene, the phytohormone which regulates plant growth.While acid 3 was aminated only in low yield and hemiacetal 4 did not submit to the Strecker synthesis, the benzophenone imine of 2-amino-4-chlorobutyronitrile 5, readily available from acrolein, did undergo quantitative base-induced cyclization smoothly under various conditions.