A Practical Synthesis of α-Amino Ketones via Aryllithium Addition to N-Boc-α-Amino Acids

Abstract

The reaction of N-Boc-α-amino acids with aryllithium reagents followed by removal of the nitrogen protecting group provides enantiomerically pure α-amino aryl ketones as their corresponding HCl salts. This practical two-step sequence gives rapid access to a pharmaceutically interesting class of compounds from commercially available starting materials.

arylations - amino acids - lithiation - ketones - nucleophilic additions

References

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<A NAME="RC02603SS-13">13</A>

Florjancic, A.; Curtin, M., unpublished results.

<A NAME="RC02603SS-14">14</A>

HPLC analysis with ChiralPak AD 4.6 × 250 mm column from Chiral Technologies. Solvent system: 25-40% EtOH in hexanes.