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Synfacts 2009(1): 0047-0047  
DOI: 10.1055/s-0028-1087397
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Diastereoselective Switch in Mannich Reactions

Contributor(s): Mark Lautens, Praew Thansandote
X.-X. Yan, Q. Peng, Q. Li, K. Zhang, J. Yao, X.-L. Hou*, Y.-D. Wu*
Shanghai Institute of Organic Chemistry and the Hong Kong University of Science and Technology, P. R. of China
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

The authors describe a copper­catalyzed asymmetric Mannich reaction of a glycine ester with various imines. Interestingly, the ­diastereoselectivity can be switched from syn to anti by replacing an electron-withdrawing ferrocenyl ligand with an electron-donating analogue. Both ligands provide Mannich products in high yields, excellent ­diastereoselectivities and excellent ee values.