Benzylic Lithiation Reaction for the Synthesis of Unnatural Amino Acids

Key words

lithiation - amino acids - carboxylation - N-Boc N-trimethyl-silylbenzylamines

Significance

Unnatural amino acids play a pivotal role in the peptide chemistry. Hence, peptide development chemists are highly attracted towards the development of new methods for the synthesis of unnatural amino acids. In 2001, Voyer and co-workers developed a new method for the synthesis of amino acids using carboxylation of lithiated N-Boc N-trimethylsilylbenzylamine derivatives.

Comment

A series of unnatural amino acids were synthesized by carboxylation of lithiated N-Boc N-trimethylsilylbenzylamine derivatives. The reaction could produce N-Boc phenylglycine derivatives with moderate optical purity in good yields. Yields and optical purities depend on the solvent, substrate, and chiral complex used in the reaction.