Combination of the structural components of amino acids with fatty acids: access to an unknown class of “fatty” α-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 class of natural products, fatty acids, is presented. By applying palladium-catalyzed amidocarbonylation, diverse new N-acyl fatty amino acids are synthesized in one step in a 100% atom-efficient manner. Utilizing a small amount (0.5 mol%) of simple commercial Pd(OAc)₂, the desired products can be synthesized in good to high yields, up to multi-g-scale. The shown products represent a combination of two essential classes of natural products and provide new bio-based building blocks with potential for many applications.