Dixon DJ,
*
Horan RAJ,
Monck NJT,
Berg P.
University of Manchester, UK
Highly Stereoselective Michael Addition Reactions of CamTHP*-Desymmetrized Glycinamide for the Synthesis of Functionally Dense Amino Acid Derivatives.
Org. Lett 2004;
6: 4427-4429
DOI:
10.1021/ol048568q
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.
