Fatty Acid and Amino Acid Derivatives in Organocatalyzed Michael Additions

TL;DR

This paper explores using fatty and amino acid derivatives in chemical reactions to create compounds with high enantioselectivity using organocatalysts.

Contribution

The study introduces a method using fatty and amino acid derivatives for efficient, high-enantioselectivity Michael additions.

Findings

Twenty compounds were synthesized with enantioselectivities up to 98% ee.

Fatty acid derivatives functioned as both nucleophiles and electrophiles.

All novel products were fully characterized and synthesized under ambient conditions.

Abstract

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.

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