A NEW AND CONVENIENT PREPARATION OF 1-AMINOCYCLOPROPANECARBOXYLIC ACID FROM ACROLEIN

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. © 1990, American Chemical Society. All rights reserved.