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 electrophile (nitroalkene acceptor). 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.
Flis et al. (Fri,) studied this question.