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Synlett 2000; 2000(11): 1565-1568
DOI: 10.1055/s-2000-7928
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A One-Pot Aza-Wittig Based Solution and Polymer Supported Route to Amines

Karl Hemming* , Matthew J. Bevan, Christina Loukou, Snahal D. Patel, Denis Renaudeau
  • *Division of Chemistry, University of Hertfordshire, Hatfield, AL10 9AB, UK; Fax +44 (0) 0 17 07 28 46 44; E-mail: k.v.hemming@herts.ac.uk
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Publication Date:
31 December 2000 (online)

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This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.

polymer supported synthesis - amines - imines - aza-Wittig reaction - iminophosphoranes