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Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-Type Reaction Using Secondary Amines, Aldehydes, and Ketene Silyl Acetals

Yusuke Tanaka, Tomoaki Hasui, Michinori Suginome*

*Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email:

Y. Tanaka, T. Hasui, M. Suginome, Synlett, 2008, 1239-1241.

DOI: 10.1055/s-2008-1072724


Mannich-rype reactions of secondary amines, aldehydes and ketene silyl acetals were efficiently promoted by catalytic amounts of diarylborinic acid esters, affording β-amino esters selectively with no formation of the corresponding β-hydroxy esters.

see article for more examples

Aminoboranes as "Compatible" Iminium Ion Generators in Aminative C-C Bond Formations

M. Suginome, L. Uehlin, M. Murakami, J. Am. Chem. Soc., 2004, 126, 13196-13197.

Key Words

boron-based catalyst, β-amino acids, iminium ion intermediate, ketene silyl acetal, nucleophilic additions, Mannich Reaction, multicomponent reactions

ID: J60-Y2008-1150