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Synthesis 2000; 2000(6): 789-800
DOI: 10.1055/s-2000-6273
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Chemoselective Reductive Amination of Aldehydes and Ketones by Dibutylchlorotin Hydride-HMPA Complex

Toshihiro Suwa* , Erika Sugiyama, Ikuya Shibata, Akio Baba
  • *Department of Molecular Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan; Fax +81 (6) 8 79 73 87; E-mail: shibata@ap.chem.eng.osaka-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Reductive amination of various aldehydes and ketones has been performed effectively by pentacoordinate chloro-substituted tin hydride complex, Bu2SnClH-HMPA. The tin reagent worked particularly well for the case using weakly basic aromatic amines as starting substrates. Stoichiometric amounts of a substrate and a reducing agent were adequate for the reaction. The Sn-Cl bond in the complex plays an important role for both steps of imine formation and subsequent reduction. Highly chemoselective reduction of carbonyls could be achieved regardless of other functionalities such as halogen, carbon-carbon double bond and hydroxyl groups in the starting carbonyls and amines.

reductive amination - aldehydes - ketones - amines - tin hydride - highly coordination

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