Fatty Acid and Amino Acid Derivatives in Organocatalyzed Michael Additions

Amino acid derivatives, such as β-keto esters and pyrrolones, were used as nucleophiles in organocatalyzed Michael additions to nitroalkene acceptors, while fatty acid derivatives acted as both nucleophiles (β-keto esters) and electrophiles (nitroalkene acceptors). Bifunctional noncovalent organocatalysts were employed as asymmetric organocatalysts. Twenty compounds-including fatty acid and amino acid derivatives, as well as fatty acid-amino acid conjugates-were prepared with enantioselectivities of up to 98% ee. All novel products were fully characterized. This research demonstrates the ease of assembling readily available fatty acid and amino acid building blocks under ambient conditions.