Combination of the structural components of amino acids with fatty acids: Access to an unknown class of “fatty” -amino acids by palladium-catalyzed amidocarbonylation

Abstract

A new class of amino acids, so-called fatty amino acids, which integrate the typical structural motif of another important type of natural products, fatty acids, is presented. Applying the palladium-catalyzed amidocarbonylation, diverse new N-acyl fatty amino acids are synthesized in one step in 100% atom-efficient manner. Utilizing small amounts (0.5 mol%) of simple commercial Pd(OAc)2 the desired products can be synthesized in good to high yields in up to multi-g-scale. The shown products represent a combination of two essential classes of natural products and provides new bio-based building blocks with potential for many applications.