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Synfacts 2013; 9(1): 0055
DOI: 10.1055/s-0032-1317845
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective Arylation of α-Imino Esters

Contributor(s):
Hisashi Yamamoto
,
Lan Luo
Chen J, Lu X, Lou W, Ye Y, Jiang H, Zeng W * South China University of Technology, Guangzhou and Chengdu Institute of Biology, P. R. of China
Palladium(II)-Catalyzed Enantioselective Arylation of α-Imino Esters.

J. Org. Chem. 2012;
77: 8541-8548
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

palladium - asymmetric arylation - arylglycine derivatives - α-amino acids

Significance

This protocol provides a practical and direct route to chiral arylglycines with high enantioselectivity (up to 99% ee). These derivatives can be easily converted into optically active α-amino acids, which are commonly used as chiral auxiliaries in asymmetric catalysis.


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Comment

A palladium(II)-catalyzed asymmetric arylation of N-aryl-α-imino esters using a chiral BOX ligand was developed. This method is applicable to various aromatic boronic acids. A stereochemical model, consistent with experimental results, suggests a re-face attack of the aryl group onto the N-arylimine carbon.


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