Ethylene Biosynthesis part 10. Synthesis and study of racemic, (1<i>R</i>, 2<i>S</i>)‐, and (1<i>S</i>, 2<i>R</i>)‐1‐Amino‐2‐(hydroxymethyl)cyclopropanecarboxylic Acid

Abstract

Abstract The preparation of optically active 1‐amino‐2‐(hydroxymethyl)cyclopropanecarboxylic acid has been achieved by a route involving cycloalkylation of dimethyl malonate with epichlorohydrin and subsequent Hofmann rearrangement. The reaction of epichlorohydrin with nucleophiles may occur al either electrophilic site, epoxide or halide. Based on the absolute configuration of the starting materials and the lactones obtained, it has been shown that the initial step of the cycloalkylation occurs at the epoxide moiety. The 1‐amino‐2‐(hydroxymethyl)‐cyclopropanecarboxylic acid, an analogue of the precursor to the plant growth hormone ethylene, is to be used in affinity purification techniques and in generation of antibodies.