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Synlett 1998; 1998(9): 967-968
DOI: 10.1055/s-1998-1838
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SmI2-Mediated Reduction of α-Functionalised Amides: Highly Enantiospecific Access to an Atropisomeric Amide

Adam D. Hughes* , Nigel S. Simpkins
  • *Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK; Fax (01 15)9 51 35 64; E-mail: Nigel.Simpkins@Nottingham.ac.uk
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Publication Date:
31 December 2000 (online)

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SmI2 or SmI2-LiCl mixtures can be used to reduce α-functionalised amides in yields of up to 85% depending upon the amide structure. The method has been applied to the synthesis of an atropisomeric anilide system in highly enantioenriched form, starting with (S)-O-acetyl lactic acid.

samarium iodide - reduction - amide - atropisomer