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

Michinori Suginome,* Lars Uehlin, and Masahiro Murakami

*Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Email: suginomesbchem.kyoto-u.ac.jp

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

DOI: 10.1021/ja045827y

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Abstract

Aminoboranes are highly efficient and mild iminium ion generators in the Mannich-type aminative coupling of aldehydes with silyl ketene acetals. The use of diisopropylaminoboranes enables a three-component Mannich reaction of free secondary amines with aldehydes and silyl ketene acetals.

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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

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

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Key Words

β-Amino Acids, Mannich Reaction, Multicomponent Reactions

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ID: J48-Y2004-1750