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Synlett 1999; 1999(12): 1987-1989
DOI: 10.1055/s-1999-2996
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Asymmetric Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagent to N-Borylimines

Shinichi Itsuno* , Ayako Yokoi, Shizue Kuroda
  • *Department of Materials Science, Toyohashi University of Technology, Toyohashi 441-8580, Japan; Fax + 81-5 32-44-68 13; E-mail: itsuno@tutms.tut.ac.jp
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Publication Date:
31 December 1999 (online)

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One pot synthesis of enantioenriched homoallylamines from nitriles is described. Chirally modified allylboron reagents reacted with N-borylimines derived from partial reduction of nitriles with LiEt3BH to afford enantioenriched homoallylamines in up to 90% ee.

N-borylimine - homoallylamine - nitrile - LiEt3BH - allylboration