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Synfacts 2009(8): 0890-0890  
DOI: 10.1055/s-0029-1217437
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Scandium-Catalyzed Enantioselective Multicomponent Mannich Reaction

Contributor(s): Mark Lautens, Praew Thansandote
S. Chen, Z. Hou, Y. Zhu, J. Wang, L. Lin, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

An enantioselective Mannich reaction consisting of an aromatic aldehyde, 2-aminophenol, and a ketene silyl acetal is described using a scandium catalyst and a ligand derived from l-ramipril. Moderate yields and good to excellent enantioselectivities can be obtained with a variety of aldehydes, particularly those bearing electron-withdrawing groups. The phenol group on the nitrogen can be removed by methylation followed by treatment with cerium ammonium nitrate, though the yield for the final step is moderate.