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Highly Enantioselective Three-Component Direct Mannich Reactions of Unfunctionalized Ketones Catalyzed by Bifunctional Organocatalysts

Qunsheng Guo and John Cong-Gui Zhao*

*Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, United States, Email: cong.zhaoutsa.edu

Q. Guo, J. C.-G. Zhao, Org. Lett., 2013, 15, 508-511.

DOI: 10.1021/ol303315c (free Supporting Information)


Abstract

A highly stereoselective three-component direct Mannich reaction between aromatic aldehydes, p-toluenesulfonamide, and unfunctionalized ketones in the presence of a bifunctional quinidine thiourea catalyst gives the corresponding N-tosylated β-aminoketones in high yields and excellent diastereo- and enantioselectivities.

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Key Words

Mannich Reaction, Multicomponent Reactions, Organocatalysis, β-amino ketones


ID: J54-Y2013-0280