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, and PRESTO, Japan Science and Technology Corporation (JST), Katsura, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2004, 126 (41), pp 13196–13197
DOI: 10.1021/ja045827y
Publication Date (Web): September 23, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, suginome@sbchem.kyoto-u.ac.jp

Abstract

Abstract Image

Aminoboranes have been shown to be highly efficient and mild iminium ion generators in the Mannich-type aminative coupling of aldehydes with silyl ketene acetals. By using aminoboranes bearing bulky amino groups, such as a diisopropylamino group, free secondary amines can be successfully used as the amino component in a three-component Mannich reaction with aldehydes and silyl ketene acetals.

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History

  • Published In Issue October 20, 2004
  • Received July 12, 2004

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