Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of α-Amino Acids and Derivatives
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Recent Literature
A Zn/Cu(OTf)2-mediated addition of alkyl bromides to
dehydroalanine (Dha) derivatives including dipeptides and tripeptides provides
selective and biocompatible access to various amino acid units in good to high
yields in an aqueous medium.
J.-A. Shin, J. Kim, H. Lee, S. Ha, H.-Y. Lee, J. Org. Chem., 2019, 84,
4558-4565.
Rhodium-catalyzed conjugate addition of potassium trifluoro(organo)borates to
dehydroalanine derivatives, using chiral ligands such as fluorophos and in situ
enantioselective protonation with guaiacol (2-methoxyphenol), afforded a variety
of protected α-amino esters with high yields and enantiomeric excesses up to
95%.
L. Navarre, R. Martinez, J.-P. Genet, S. Darses, J. Am. Chem. Soc., 2008,
130, 6159-6169.
Potassium trifluoro(organo)borates, which are highly stable and easily
prepared organoboron derivatives, were able to react with various
dehydroamino esters to alanine derivatives in good to high yields. This
reaction, catalyzed by rhodium complexes, tolerates a great variety of amino
protecting groups.
L. Navarre, S. Darses, J.-P. Genet, Eur. J. Org. Chem., 2004,
69-73.
