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Addition of allylzinc to α-amino acid-derived imines: synthesis of diamino alcohols by hydroboration

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Abstract

Imines obtained by condensation of Z-protected or Boc-protected α-amino aldehydes with α-amino tert-butyl esters or with O-silyl-protected amino alcohols were reacted with preformed allyl zinc yielding homoallylamines with yields around 50% and selectivities ranging from 50:50 to 90:10. Hydroboration of the terminal double bond furnished diamino alcohols with yields up to 97%. The configuration of the substrates was determined by X-ray-crystallographic analysis of a hydroboration product and comparison of physical data.

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Authors and Affiliations

  1. Karlsruher Institut für Technologie (KIT), Institut für Organische Chemie, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany

    Mickael Virlouvet & Joachim Podlech

  2. Karlsruher Institut für Technologie (KIT), Institut für Anorganische Chemie, Engesserstraße 15, 76131, Karlsruhe, Germany

    Helmut Goesmann & Claus Feldmann

Authors
  1. Mickael Virlouvet
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  2. Helmut Goesmann
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  3. Claus Feldmann
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  4. Joachim Podlech
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Correspondence to Joachim Podlech.

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Virlouvet, M., Goesmann, H., Feldmann, C. et al. Addition of allylzinc to α-amino acid-derived imines: synthesis of diamino alcohols by hydroboration. Monatsh Chem 141, 177–198 (2010). https://doi.org/10.1007/s00706-009-0239-y

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  • DOI: https://doi.org/10.1007/s00706-009-0239-y

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