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Synthesis 2003(11): 1653-1656
DOI: 10.1055/s-2003-40875
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Alan S. Florjancic*, George S. Sheppard
Abbott Laboratories, Global Pharmaceutical Products Research and Development, R4PM AP10, 100 Abbott Park Road, Abbott Park, IL 60064, USA
Fax: +1(847)9355466; e-Mail: alan.florjancic@abbott.com;
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Publication History

Received 7 May 2003
Publication Date:
25 July 2003 (online)

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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.

Key words

arylations - amino acids - lithiation - ketones - nucleophilic additions

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Florjancic, A.; Curtin, M., unpublished results.

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