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Synlett 2009(18): 2953-2956  
DOI: 10.1055/s-0029-1218266
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Access to α-Functionalized Glycine Derivatives with Arylboronic Acid via Imino Amides

Liang Zhao, Xiaohong Liao, Chao-Jun Li*
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
Fax: +1(514)3983797; e-Mail: cj.li@McGill.ca;
Further Information

Publication History

Received 4 August 2009
Publication Date:
08 October 2009 (online)

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Abstract

An efficient approach was developed for the α-arylation of imino amides with arylboronic acids. Different substrates were examined for this arylation reaction. For the α-arylation of N-phenylimino amide, due to the electron-withdrawing properties of the phenyl group, the tautomerization between the amide and the iminol is more difficult. Thus, low reaction rate and low conversion were observed. This phenomenon supported our previously proposed mechanism for the arylation of α-amino acid derivatives. Meanwhile, this method provides an alternative approach for the synthesis of α-functionalized glycine derivatives.

Key words

α-functionalization - arylation - iminol - imino amide - glycine derivatives

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