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Organic & Biomolecular Chemistry

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Org. Biomol. Chem., 2007, 5, 1018 - 1020, DOI: 10.1039/b701579h


Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system

Lili Cheng, Xiaoyu Wu and Yixin Lu


The direct three-component Mannich reactions of O-benzyl hydroxyacetone with p-anisidine and aromatic or aliphatic aldehydes in the presence of an L-threonine-derived catalyst afforded anti-1,2-amino alcohols in good-to-excellent yields and with enantioselectivities of up to 97%. This study is the first demonstration that direct three-component Mannich reactions can be promoted by a primary amino acid in water.

Graphical abstract image for this article  (ID: b701579h)