Stereoselective Michael Addition Reaction for Synthesis of Unnatural Amino Acids

Keywords

unnatural amino acids - Michael addition reaction - stereoselective synthesis - glycinamides

Significance

Unnatural amino acids are vital building blocks for the synthesis of complex natural products, biologically active molecules, and peptides. In this context, the authors developed a stereoselective Michael addition reaction of camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide with nitro-olefins, α,β-unsaturated ketones, esters, and lactones for the synthesis of unnatural amino acids.

Comment

A series of unnatural amino acids were synthesized using the developed method. The reaction is highly stereoselective and the product unnatural amino acids were transformed for the synthesis of 3-substituted pyroglutamides.

Publication History

Article published online:
21 November 2024