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Protecting-Group-Free Synthesis of Amines: Synthesis of Primary Amines from Aldehydes via Reductive Amination

Emma M. Dangerfield, Catherine H. Plunkett, Anna L. Win-Mason, Bridget L. Stocker and Mattie S. M. Timmer

*School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand, Email: mattie.timmervuw.ac.nz

E. M. Dangerfield, C. H. Plunkett, A. L. Win-Mason, B. L. Stocker, M. S. M. Timmer, J. Org. Chem., 2010, 75, 5470-5477.

DOI: 10.1021/jo100004c (free Supporting Information)


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Abstract

By optimizing the metal hydride/ammonia mediated reductive amination of aldehydes and hemiacetals, primary amines were selectively prepared with no or minimal formation of the usual secondary and tertiary amine byproduct. The methodology was performed on a range of functionalized aldehyde substrates, including in situ formed aldehydes from a Vasella reaction.

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Key Words

reductive amination, primary amines, sodium cyanoborohydride


ID: J42-Y2010-2270