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Synfacts 2008(4): 0390-0390  
DOI: 10.1055/s-2008-1042797
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed One-Pot Enantioselective Synthesis of Arylglycines

Contributor(s): Mark Lautens, Praew Thansandote
H. Dai, M. Yang, X. Lu*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

A palladium-catalyzed one-pot enantioselective synthesis of arylglycines has been developed from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids. A good scope of arylboronic acids can be used, including electron-withdrawing and electron-donating examples. The imino esters were prepared in situ by a [2+2] cycloaddition and were inspired by Holmes and co-workers (P. Hamley, A. B. Holmes, A. Kee, T. Ladduwahetty, D. F. Smith Synlett 1999, 29).